Benzenepropanoyl chloride → N-(3-phenylpropionyl)-D,L-alanine Isobutyl Ester

HRID 1859104Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:13]([O:17][C:18](=[O:22])[CH:19]([CH3:21])[NH2:20])[CH:14]([CH3:16])[CH3:15]>>[CH2:13]([O:17][C:18](=[O:22])[CH:19]([CH3:21])[NH:20][C:9](=[O:10])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:14]([CH3:16])[CH3:15]

Participants

Reactant 2

HCID 64801Benzenepropanoyl chloride

HCID 862001092-Methylpropyl 2-aminopropanoate hydrochloride

Product 1

HCID 15480461N-(3-phenylpropionyl)-D,L-alanine Isobutyl Ester

Procedure

Following General Procedure A' above and using 3-phenylpropionyl chloride (Aldrich) and D,L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of from 51°-54° C. The reaction was monitored by tlc on silica gel and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl.

Sources & evidence

ORD record: ord-d65e58a4480c48e3ac641203b6f0219f
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153652

Reaction notes

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