(S)-Benzyl 3-(4-hy­droxy­phen­yl)-2-(trityl­amino)­propano­ate

Meimei Chen; Xinmei Lai; Changen Zhou; Xuemei Yang

doi:10.1107/S1600536811017351

. 2011 May 14;67(Pt 6):o1412. doi: 10.1107/S1600536811017351

(S)-Benzyl 3-(4-hydroxyphenyl)-2-(tritylamino)propanoate

Meimei Chen ^a, Xinmei Lai ^a, Changen Zhou ^a, Xuemei Yang ^a,^*

PMCID: PMC3120518 PMID: 21754794

Abstract

The title compound, C₃₅H₃₁NO₃, was obtained by the reaction of (S)-benzyl 2-amino-3-(4-hydroxyphenyl)propanoate and (chloromethanetriyl)tribenzene. The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. In the crystal, molecules are linked into chains running along the a axis by intermolecular O—H⋯O hydrogen bonds.

Related literature

For the synthesis and the physiological role of isodityrosine, see: Skaff et al. (2005 ▶). For the structure of the NH₂ analogue of the title compound, (S)-benzyl 2-amino-3-(4-hydroxyphenyl)propanoate, see: Luo et al. (2009 ▶).

Experimental

Crystal data

C₃₅H₃₁NO₃
M _r = 513.61
Orthorhombic,
a = 9.1188 (18) Å
b = 15.774 (3) Å
c = 19.393 (4) Å
V = 2789.4 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.32 × 0.25 × 0.11 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.976, T _max = 0.991
24111 measured reflections
3097 independent reflections
2200 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.093
S = 1.09
3097 reflections
356 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017351/zq2100sup1.cif

e-67-o1412-sup1.cif^{(26.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017351/zq2100Isup2.hkl

e-67-o1412-Isup2.hkl^{(152KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017351/zq2100Isup3.cml

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
O3—H3A⋯O1ⁱ	0.82	1.95	2.772 (3)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefully acknowledge financial support by the Fujian Provincial Department of Education project (JA09130) and the Fujian Provincial Health Department Special Project (wzzsj0901).

supplementary crystallographic information

Comment

The title compound is an important intermediate in the synthesis of isodityrosine, which occurs in plant cell wall proteins and presumably conveys a strengthening and/or defensive role to the proteins (Skaff et al., 2005). The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles in the compound are comparable to those reported for a similar compound (Luo et al., 2009). The dihedral angle between the C18-phenyl and C24-phenyl, C18-phenyl and C30-phenyl, C24-phenyl and C30-phenyl planes are 80.2 (1), 61.9 (1) and 65.4 (1)°, respectively. The crystal packing is stabilized by strong O—H···O intermolecular hydrogen-bonding interactions involving the hydroxyl group which link the molecules into a chain running along the a axis (Table 1).

Experimental

To a solution of (S)-benzyl 2-amino-3-(4-hydroxyphenyl)propanoate (0.68 g, 2.5 mmol), and (chloromethanetriyl)tribenzene (0.70 g, 2.5 mmol) in acetonitrile (8 ml) at 273 K was added dropwise triethylamine (0.40 g, 4 mmol). The cooling bath was removed and the mixture warmed to ambient temperature for 2 h. The solvent was removed and the crude product was purified by column chromatography (petroleum ether-ethyl acetate, 4:1) to give the title compound (I) as a white solid in 85% yield. Single crystals of (I) were obtained by slow evaporation of a petroleum ether/ethyl acetate solution (6:1 v/v).