Phenylacetyl chloride → N-(phenylacetyl)-D,L-alanine iso-butyl ester

HRID 636087Notes

Reaction equation

[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:12]([O:16][C:17](=[O:21])[CH:18]([CH3:20])[NH2:19])[CH:13]([CH3:15])[CH3:14]>>[CH2:12]([O:16][C:17](=[O:21])[CH:18]([CH3:20])[NH:19][C:8](=[O:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:13]([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 7679Phenylacetyl chloride

HCID 862001092-Methylpropyl 2-aminopropanoate hydrochloride

Product 1

HCID 9903374N-(phenylacetyl)-D,L-alanine iso-butyl ester

Procedure

Following General Procedure A′ above and using phenylacetyl chloride (Aldrich) and D,L-alanine iso-butyl ester hydrochloride (from Example B′ above), the title compound was prepared. 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-33e9c1de131547b3a4b978d639b5a8b1
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06191166B1

Reaction notes

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