Methyl 2-(2-{[(benz­yloxy)carbon­yl]amino}­propan-2-yl)-5-hy­droxy-6-meth­oxy­pyrimidine-4-carboxyl­ate

Shang, Z.; Qi, S.; Tao, X.; Zhang, G.

doi:10.1107/S160053681101628X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1335

doi:10.1107/S160053681101628X

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Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-methoxypyrimidine-4-carboxylate

Zhenhua Shang,^a ^* Shan Qi,^a Xiao Tao ^a and Guangbo Zhang ^a

^aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: zhenhuashang@yahoo.com.cn

(Received 3 April 2011; accepted 29 April 2011; online 7 May 2011)

In the title compound, C₁₈H₂₁N₃O₆, the dihedral angle between the two aromatic rings is 61.1 (1)°. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds. An intramolecular O—H⋯O hydrogen bonds is also present.

Related literature

The title compound was obtained in an attempt to synthesise an intermediate for the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide], see: Belyk et al. (2006). For background to raltegravir, see: Steigbigel et al. (2008 ). For related structures, see: Shang & Shang (2007 ); Fun et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₁N₃O₆
M_r = 375.38
Monoclinic, P 2₁
a = 8.5313 (17) Å
b = 6.5413 (13) Å
c = 16.167 (3) Å
β = 97.37 (3)°
V = 894.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.979, T_max = 0.987
7509 measured reflections
2281 independent reflections
1854 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.088
S = 1.01
2281 reflections
256 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.87 (3)	2.27 (3)	2.889 (2)	128 (2)
O2—H2⋯O3	0.87 (3)	1.95 (3)	2.652 (2)	136 (3)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101628X/hg5023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101628X/hg5023Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101628X/hg5023Isup3.cml

checkCIF report

Comment top

Raltegravir (MK-0518, brand name Isentress) is an antiretroviral drug produced by Merck & Co, used to treat HIV infection (Steigbigel et al., 2008). It received FDA approval in October 2007, the first of a new class of HIV drugs, the integrase inhibitors, to receive such approval. When methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate was reacted with dimethyl sulfate catalyzed by magnesium methoxide in dimethyl sulfoxide (Belyk et al., 2006), as we designed, in order to synthesize methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate as the key intermediate of Raltegravir, two products appeared on thin layer chromatography. These products were separated through flash chromatography and the structures were conformed by nuclear magnetic resonance and X-ray analysis. The result showed that the title compound was the byproduct of the reaction. The pyrimidinone ring is planar, as it is in a related compound (Fun et al., 2009). This is in contrast with another related compound (Shang et al., 2007), where the heterocyclic ring is twisted. In the title compound the dihedral angle between the two aromatic rings is 118.9 (1)°. The crystal structure is stabilized through intermolecular O—H···O hydrogen bonds; intramolecular O—H···O hydrogen bonds are also present.

Related literature top

The title compound was obtained in an attempt to synthesise an intermediate for the the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide], see: Belyk et al. (2006). For background to raltegravir, see: Steigbigel et al. (2008). For related structures, see: Shang & Shang (2007); Fun et al. (2009).

Experimental top

To a slurry of methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.5 g) and magnesium methoxide (2.1 g) in dimethyl sulfoxide(15 ml) at 70 °C, dimethyl sulfate (3.1 g) was added dropwise. After addition, the mixture was heated at the same temperature for 8 h. To the reaction mixture was then added 40 ml 2 N HCl and then 100 ml water. Solid appeared when the mixture was stirred in an ice-water bath. The products were filtered and separated by flash chromatography. 50 mg of the title compound was dissolved in 30 ml methanol and the solution was kept at room temperature for 10 d; natural evaporation gave colorless single crystals of the title compound suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.

Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)- 5-hydroxy-6-methoxypyrimidine-4-carboxylate top

Crystal data top

C₁₈H₂₁N₃O₆	F(000) = 396
M_r = 375.38	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3543 reflections
a = 8.5313 (17) Å	θ = 2.3–27.5°
b = 6.5413 (13) Å	µ = 0.11 mm⁻¹
c = 16.167 (3) Å	T = 113 K
β = 97.37 (3)°	Plate, colorless
V = 894.7 (3) Å³	0.20 × 0.16 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2281 independent reflections
Radiation source: rotating anode	1854 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.044
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω and ϕ scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −7→8
T_min = 0.979, T_max = 0.987	l = −21→20
7509 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0491P)²] where P = (F_o² + 2F_c²)/3
2281 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₂₁N₃O₆	V = 894.7 (3) Å³
M_r = 375.38	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.5313 (17) Å	µ = 0.11 mm⁻¹
b = 6.5413 (13) Å	T = 113 K
c = 16.167 (3) Å	0.20 × 0.16 × 0.12 mm
β = 97.37 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2281 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1854 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.987	R_int = 0.044
7509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.25 e Å⁻³
2281 reflections	Δρ_min = −0.21 e Å⁻³
256 parameters

Special details top

Experimental. 1H-NMR (500 MHz, CDCl3) 1.72(s, 6H), 3.66(s, 3H), 3.97(s, 3H), 5.03(s, 2H), 5.28 (s, 1H), 7.02–7.32(m, 5H, J=75 Hz), 10.39(s, 1H).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.7129 (2)	0.6028 (3)	0.89047 (10)	0.0184 (4)
N2	0.4395 (2)	0.6250 (3)	0.83861 (10)	0.0192 (4)
N3	0.4877 (2)	0.4973 (3)	0.68708 (11)	0.0210 (4)
H3	0.427 (3)	0.599 (5)	0.6595 (17)	0.043 (8)*
O1	0.25348 (16)	0.6638 (3)	0.92818 (9)	0.0220 (4)
O2	0.46916 (18)	0.6583 (3)	1.06058 (9)	0.0219 (4)
H2	0.547 (3)	0.670 (6)	1.1011 (18)	0.050 (9)*
O3	0.77719 (17)	0.6582 (3)	1.11167 (8)	0.0244 (4)
O4	0.94697 (16)	0.6036 (3)	1.01878 (9)	0.0231 (4)
O5	0.4667 (2)	0.2009 (2)	0.76039 (9)	0.0259 (4)
O6	0.26425 (19)	0.3210 (3)	0.66809 (10)	0.0287 (4)
C1	0.5941 (2)	0.6005 (3)	0.82953 (12)	0.0185 (5)
C2	0.4043 (2)	0.6444 (3)	0.91420 (12)	0.0183 (4)
C3	0.5207 (2)	0.6435 (3)	0.98553 (12)	0.0174 (4)
C4	0.6744 (2)	0.6263 (3)	0.96913 (12)	0.0174 (4)
C5	0.1359 (2)	0.6528 (4)	0.85502 (12)	0.0240 (5)
H5A	0.1437	0.7746	0.8205	0.036*
H5B	0.0302	0.6460	0.8725	0.036*
H5C	0.1544	0.5304	0.8227	0.036*
C6	0.8042 (2)	0.6304 (4)	1.04017 (12)	0.0193 (4)
C7	1.0779 (3)	0.6187 (4)	1.08615 (13)	0.0258 (5)
H7A	1.0933	0.7620	1.1029	0.039*
H7B	1.1745	0.5663	1.0669	0.039*
H7C	1.0537	0.5379	1.1340	0.039*
C8	0.6296 (3)	0.5754 (3)	0.73967 (13)	0.0197 (5)
C9	0.7695 (3)	0.4322 (4)	0.73342 (14)	0.0261 (6)
H9A	0.7435	0.2947	0.7515	0.039*
H9B	0.8627	0.4831	0.7693	0.039*
H9C	0.7920	0.4271	0.6755	0.039*
C10	0.6641 (3)	0.7866 (4)	0.70588 (15)	0.0285 (6)
H10A	0.6796	0.7750	0.6470	0.043*
H10B	0.7600	0.8422	0.7378	0.043*
H10C	0.5749	0.8780	0.7111	0.043*
C11	0.4121 (3)	0.3289 (4)	0.71076 (12)	0.0211 (5)
C12	0.1749 (3)	0.1388 (4)	0.67933 (14)	0.0313 (6)
H12A	0.0616	0.1746	0.6762	0.038*
H12B	0.2092	0.0820	0.7355	0.038*
C13	0.1953 (3)	−0.0221 (4)	0.61451 (14)	0.0248 (5)
C14	0.3061 (3)	−0.0041 (5)	0.55949 (14)	0.0322 (6)
H14	0.3742	0.1112	0.5625	0.039*
C15	0.3181 (3)	−0.1545 (5)	0.49977 (15)	0.0399 (7)
H15	0.3942	−0.1411	0.4621	0.048*
C16	0.2197 (4)	−0.3238 (5)	0.49494 (16)	0.0427 (7)
H16	0.2290	−0.4268	0.4544	0.051*
C17	0.1087 (3)	−0.3423 (5)	0.54905 (15)	0.0379 (7)
H17	0.0401	−0.4572	0.5455	0.046*
C18	0.0970 (3)	−0.1928 (4)	0.60889 (14)	0.0293 (6)
H18	0.0209	−0.2072	0.6465	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0175 (9)	0.0203 (10)	0.0177 (8)	0.0002 (8)	0.0028 (7)	−0.0018 (7)
N2	0.0165 (9)	0.0218 (9)	0.0190 (8)	0.0010 (8)	0.0020 (7)	−0.0023 (8)
N3	0.0206 (10)	0.0237 (10)	0.0178 (9)	0.0015 (8)	−0.0011 (7)	0.0003 (8)
O1	0.0129 (8)	0.0321 (9)	0.0211 (7)	0.0017 (7)	0.0021 (6)	−0.0023 (7)
O2	0.0196 (8)	0.0282 (9)	0.0176 (7)	0.0007 (7)	0.0020 (6)	−0.0022 (7)
O3	0.0215 (8)	0.0348 (10)	0.0170 (7)	0.0017 (8)	0.0035 (6)	−0.0023 (7)
O4	0.0126 (8)	0.0357 (10)	0.0209 (7)	−0.0004 (7)	0.0014 (6)	−0.0023 (7)
O5	0.0303 (10)	0.0250 (9)	0.0225 (8)	0.0032 (7)	0.0037 (7)	0.0021 (7)
O6	0.0249 (9)	0.0295 (9)	0.0295 (8)	−0.0040 (8)	−0.0044 (7)	−0.0018 (7)
C1	0.0180 (11)	0.0182 (11)	0.0193 (10)	0.0003 (9)	0.0024 (8)	−0.0012 (8)
C2	0.0161 (11)	0.0153 (11)	0.0236 (10)	0.0004 (9)	0.0032 (8)	−0.0011 (9)
C3	0.0208 (11)	0.0141 (10)	0.0174 (9)	−0.0015 (9)	0.0026 (8)	−0.0019 (8)
C4	0.0174 (11)	0.0164 (10)	0.0182 (9)	−0.0007 (9)	0.0017 (8)	−0.0012 (8)
C5	0.0176 (11)	0.0316 (13)	0.0214 (11)	0.0008 (10)	−0.0028 (8)	−0.0020 (10)
C6	0.0200 (11)	0.0191 (11)	0.0184 (10)	−0.0026 (10)	0.0009 (8)	−0.0002 (9)
C7	0.0190 (12)	0.0376 (14)	0.0196 (10)	−0.0044 (11)	−0.0016 (9)	0.0005 (10)
C8	0.0168 (11)	0.0253 (12)	0.0169 (10)	0.0001 (9)	0.0010 (8)	−0.0015 (8)
C9	0.0196 (13)	0.0385 (14)	0.0199 (11)	0.0036 (10)	0.0012 (9)	−0.0043 (10)
C10	0.0291 (14)	0.0307 (13)	0.0266 (12)	−0.0061 (11)	0.0073 (10)	0.0002 (10)
C11	0.0222 (12)	0.0257 (12)	0.0157 (10)	0.0002 (10)	0.0037 (9)	−0.0054 (9)
C12	0.0270 (13)	0.0359 (15)	0.0317 (12)	−0.0110 (12)	0.0068 (10)	−0.0065 (12)
C13	0.0214 (12)	0.0316 (13)	0.0204 (10)	−0.0016 (10)	−0.0009 (9)	0.0004 (9)
C14	0.0267 (14)	0.0426 (16)	0.0269 (12)	−0.0030 (12)	0.0021 (10)	−0.0024 (11)
C15	0.0376 (16)	0.056 (2)	0.0256 (12)	0.0101 (15)	0.0042 (11)	−0.0030 (13)
C16	0.0589 (19)	0.0398 (17)	0.0267 (13)	0.0142 (15)	−0.0054 (13)	−0.0064 (12)
C17	0.0522 (17)	0.0255 (13)	0.0324 (13)	−0.0012 (13)	−0.0088 (12)	0.0023 (11)
C18	0.0325 (14)	0.0309 (14)	0.0231 (11)	−0.0050 (11)	−0.0020 (10)	0.0032 (10)

Geometric parameters (Å, º) top

N1—C1	1.320 (2)	C7—H7B	0.9800
N1—C4	1.363 (3)	C7—H7C	0.9800
N2—C2	1.301 (3)	C8—C10	1.528 (3)
N2—C1	1.355 (3)	C8—C9	1.531 (3)
N3—C11	1.357 (3)	C9—H9A	0.9800
N3—C8	1.478 (3)	C9—H9B	0.9800
N3—H3	0.92 (3)	C9—H9C	0.9800
O1—C2	1.341 (2)	C10—H10A	0.9800
O1—C5	1.451 (2)	C10—H10B	0.9800
O2—C3	1.346 (3)	C10—H10C	0.9800
O2—H2	0.87 (3)	C12—C13	1.511 (3)
O3—C6	1.221 (2)	C12—H12A	0.9900
O4—C6	1.320 (3)	C12—H12B	0.9900
O4—C7	1.460 (2)	C13—C14	1.384 (3)
O5—C11	1.211 (3)	C13—C18	1.392 (4)
O6—C11	1.358 (3)	C14—C15	1.391 (4)
O6—C12	1.438 (3)	C14—H14	0.9500
C1—C8	1.530 (3)	C15—C16	1.386 (5)
C2—C3	1.422 (3)	C15—H15	0.9500
C3—C4	1.375 (3)	C16—C17	1.375 (4)
C4—C6	1.490 (3)	C16—H16	0.9500
C5—H5A	0.9800	C17—C18	1.388 (4)
C5—H5B	0.9800	C17—H17	0.9500
C5—H5C	0.9800	C18—H18	0.9500
C7—H7A	0.9800

C1—N1—C4	116.32 (18)	C1—C8—C9	112.28 (18)
C2—N2—C1	117.25 (17)	C8—C9—H9A	109.5
C11—N3—C8	120.17 (17)	C8—C9—H9B	109.5
C11—N3—H3	117.4 (18)	H9A—C9—H9B	109.5
C8—N3—H3	113.6 (19)	C8—C9—H9C	109.5
C2—O1—C5	115.85 (16)	H9A—C9—H9C	109.5
C3—O2—H2	112 (2)	H9B—C9—H9C	109.5
C6—O4—C7	116.03 (16)	C8—C10—H10A	109.5
C11—O6—C12	116.08 (19)	C8—C10—H10B	109.5
N1—C1—N2	125.66 (19)	H10A—C10—H10B	109.5
N1—C1—C8	118.88 (18)	C8—C10—H10C	109.5
N2—C1—C8	115.42 (17)	H10A—C10—H10C	109.5
N2—C2—O1	120.61 (17)	H10B—C10—H10C	109.5
N2—C2—C3	122.69 (19)	O5—C11—N3	126.3 (2)
O1—C2—C3	116.69 (18)	O5—C11—O6	124.3 (2)
O2—C3—C4	127.57 (18)	N3—C11—O6	109.39 (18)
O2—C3—C2	117.10 (18)	O6—C12—C13	112.31 (19)
C4—C3—C2	115.33 (18)	O6—C12—H12A	109.1
N1—C4—C3	122.66 (17)	C13—C12—H12A	109.1
N1—C4—C6	118.47 (18)	O6—C12—H12B	109.1
C3—C4—C6	118.86 (18)	C13—C12—H12B	109.1
O1—C5—H5A	109.5	H12A—C12—H12B	107.9
O1—C5—H5B	109.5	C14—C13—C18	118.8 (2)
H5A—C5—H5B	109.5	C14—C13—C12	122.4 (2)
O1—C5—H5C	109.5	C18—C13—C12	118.8 (2)
H5A—C5—H5C	109.5	C13—C14—C15	120.2 (3)
H5B—C5—H5C	109.5	C13—C14—H14	119.9
O3—C6—O4	124.10 (18)	C15—C14—H14	119.9
O3—C6—C4	121.35 (19)	C16—C15—C14	120.4 (3)
O4—C6—C4	114.55 (17)	C16—C15—H15	119.8
O4—C7—H7A	109.5	C14—C15—H15	119.8
O4—C7—H7B	109.5	C17—C16—C15	119.7 (3)
H7A—C7—H7B	109.5	C17—C16—H16	120.1
O4—C7—H7C	109.5	C15—C16—H16	120.1
H7A—C7—H7C	109.5	C16—C17—C18	119.9 (3)
H7B—C7—H7C	109.5	C16—C17—H17	120.0
N3—C8—C10	106.74 (17)	C18—C17—H17	120.0
N3—C8—C1	109.65 (18)	C17—C18—C13	120.9 (3)
C10—C8—C1	108.25 (18)	C17—C18—H18	119.5
N3—C8—C9	109.79 (19)	C13—C18—H18	119.5
C10—C8—C9	110.0 (2)

C4—N1—C1—N2	2.0 (3)	C11—N3—C8—C10	−168.3 (2)
C4—N1—C1—C8	179.8 (2)	C11—N3—C8—C1	−51.3 (3)
C2—N2—C1—N1	−2.9 (3)	C11—N3—C8—C9	72.5 (3)
C2—N2—C1—C8	179.2 (2)	N1—C1—C8—N3	158.04 (19)
C1—N2—C2—O1	−178.2 (2)	N2—C1—C8—N3	−23.9 (3)
C1—N2—C2—C3	0.9 (3)	N1—C1—C8—C10	−85.9 (2)
C5—O1—C2—N2	2.5 (3)	N2—C1—C8—C10	92.1 (2)
C5—O1—C2—C3	−176.63 (19)	N1—C1—C8—C9	35.7 (3)
N2—C2—C3—O2	−177.9 (2)	N2—C1—C8—C9	−146.3 (2)
O1—C2—C3—O2	1.2 (3)	C8—N3—C11—O5	−19.5 (3)
N2—C2—C3—C4	1.7 (3)	C8—N3—C11—O6	162.23 (18)
O1—C2—C3—C4	−179.13 (19)	C12—O6—C11—O5	−5.0 (3)
C1—N1—C4—C3	1.0 (3)	C12—O6—C11—N3	173.27 (18)
C1—N1—C4—C6	−179.9 (2)	C11—O6—C12—C13	−92.1 (2)
O2—C3—C4—N1	176.9 (2)	O6—C12—C13—C14	9.1 (3)
C2—C3—C4—N1	−2.7 (3)	O6—C12—C13—C18	−169.70 (19)
O2—C3—C4—C6	−2.2 (3)	C18—C13—C14—C15	0.1 (3)
C2—C3—C4—C6	178.2 (2)	C12—C13—C14—C15	−178.7 (2)
C7—O4—C6—O3	−2.9 (3)	C13—C14—C15—C16	−0.2 (4)
C7—O4—C6—C4	176.54 (19)	C14—C15—C16—C17	0.6 (4)
N1—C4—C6—O3	177.4 (2)	C15—C16—C17—C18	−0.8 (4)
C3—C4—C6—O3	−3.5 (3)	C16—C17—C18—C13	0.7 (4)
N1—C4—C6—O4	−2.1 (3)	C14—C13—C18—C17	−0.4 (3)
C3—C4—C6—O4	177.1 (2)	C12—C13—C18—C17	178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.87 (3)	2.27 (3)	2.889 (2)	128 (2)
O2—H2···O3	0.87 (3)	1.95 (3)	2.652 (2)	136 (3)

Symmetry code: (i) −x+1, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃O₆
M_r	375.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	8.5313 (17), 6.5413 (13), 16.167 (3)
β (°)	97.37 (3)
V (Å³)	894.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.979, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7509, 2281, 1854
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.088, 1.01
No. of reflections	2281
No. of parameters	256
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.87 (3)	2.27 (3)	2.889 (2)	128 (2)
O2—H2···O3	0.87 (3)	1.95 (3)	2.652 (2)	136 (3)

Symmetry code: (i) −x+1, y+1/2, −z+2.

Acknowledgements

The authors thank the funds of Hebei Province Science and Technology Research and Development Projects (No. 08276409D) and Hebei University of Science and Technology.

References

Belyk, M., Morrison, G. & Jones, P. (2006). Patent No. WO200606712. Google Scholar
Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Balasubramani, K., Hazra, A., Kumar Das, M. & Goswami, S. (2009). Acta Cryst. E65, o1484–o1485. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shang, Z.-H. & Shang, Q. (2007). Acta Cryst. E63, o2280–o2281. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steigbigel, et al. (2008). N. Engl. J. Med. 359, 339–354. Web of Science CrossRef PubMed Google Scholar

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Volume 67| Part 6| June 2011| Page o1335

doi:10.1107/S160053681101628X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 2-(2-{[(benz­yl­oxy)carbon­yl]amino}­propan-2-yl)-5-hy­dr­oxy-6-meth­­oxy­pyrimidine-4-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-methoxypyrimidine-4-carboxylate