4-(4-Ethoxy­benz­yl)-1,3-oxazolidin-2-one

Hong-Yong Wang; Min-Hao Xie; Shi-Neng Luo; Yong-Jun He; Pei Zou

doi:10.1107/S160053680900957X

. 2009 Mar 19;65(Pt 4):o805. doi: 10.1107/S160053680900957X

4-(4-Ethoxybenzyl)-1,3-oxazolidin-2-one

Hong-Yong Wang ^a, Min-Hao Xie ^a,^*, Shi-Neng Luo ^a, Yong-Jun He ^a, Pei Zou ^a

PMCID: PMC2968907 PMID: 21582528

Abstract

In the title compound, C₁₂H₁₅NO₃, the ethoxybenzyl ring plane forms a dihedral angle of 60.3 (4)° with the mean plane of the oxazolidine ring. The molecules are linked through N—H⋯O hydrogen bonds into a chain running in the b direction.

Related literature

For background literature, see: Chrzanowska & Rozwadowska (2004 ▶); Rozwadowska (1994 ▶); Scott & Williams (2002 ▶); Tussetschläger et al. (2007 ▶).

Experimental

Crystal data

C₁₂H₁₅NO₃
M _r = 221.25
Orthorhombic,
a = 5.7960 (12) Å
b = 9.924 (2) Å
c = 20.209 (4) Å
V = 1162.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989 ▶) T _min = 0.973, T _max = 0.991
2427 measured reflections
1246 independent reflections
904 reflections with I > 2σ(I)
R _int = 0.043
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.150
S = 1.01
1246 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900957X/pv2144sup1.cif

e-65-0o805-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900957X/pv2144Isup2.hkl

e-65-0o805-Isup2.hkl^{(61.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O3ⁱ	0.86	1.99	2.845 (4)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from Jiangsu Institute of Nuclear Medicine.

supplementary crystallographic information

Comment

Tetrahydroisoquinoline alkaloids have received much interest because of their tremendous structural diversity and broad spectrum of biological and pharmaceutical activities (Rozwadowska, 1994; Scott & Williams, 2002; Chrzanowska & Rozwadowska, 2004). As part of our own work in this area, we prepared the title compound, (I), as an intermediate in the synthesis of tyrosine-derived N-[(phenylsulfonyl)alkyl]oxazolidinones as an extension of Petrini's methodology (Tussetschläger, et al., 2007). The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the mean planes of the C1 - C9/O1 ethoxybenzyl ring and the C10/N/C12/O2/C11/O3 oxazolidine ring is 60.3 (4)°. In the crystal structure, adjacent molecules are linked through N—H···O type hydrogen-bonding interactions resulting in chains running in the b direction (Table 1). The structure also contains non-classical hydrogen bonds of the type C—H···O linking the molecules into chains along the a-axis.

Experimental

Sodium borohydride was added to a solution of 2-(tert-butoxycarbonylamino)-3-(4-ethoxyphenyl)propanoic acid (3.09 g, 10 mmol) in tetrahydrofuran (50 ml). Then methanol (5 ml) was slowly added to the resulting suspension and the temperature kept below 243 K. After the mixture was stirred for 1 h at room temperature, the excess reagent was destroyed by addition of acetic acid (1 ml). The solvent was evaporated, and the oily residue was diluted with water (50 ml) and extracted three times with ethyl acetate (25 ml) each. The combined organic extracts were wash with brine, dried with sodium sulfate, and concentrated in vacuo. The crude tert-butyl 1-(4-ethoxyphenyl)-3- hydroxypropan-2-ylcarbamate was obtained 2.7 g. Then tert-butyl 1- (4-ethoxyphenyl)-3-hydroxypropan-2-ylcarbamate (2.7 g) in THF (50 ml) was added to a suspension of sodium hydride (0.92 g, 23 mmol) in THF (120 ml) over a period of 20 min, stirred for 12 h, then quenched with a saturated solution of aqueous ammonium chloride (45 ml). The reaction mixture was then extracted three times with ethyl acetate (25 ml) each, the organic layers combined, washed with aqueous hydrochloric acid (60 ml, 5% solution), saturated NaHCO₃ solution (60 ml), and brine (60 ml), and then dried over sodium sulfate. The solvent was then removed in vacuo to yield the title compound (1.81 g, 8.2 mmol) as a white solid. The title compound was crystalized by slow evaporation of a solution in methanol.