Phenylacetyl chloride → N-(phenylacetyl)-L-alanine isobutyl ester

HRID 1385666Notes

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])[C@H:18]([CH3:20])[NH2:19])[CH:13]([CH3:15])[CH3:14]>>[CH2:12]([O:16][C:17](=[O:21])[C@H: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 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 15480460N-(phenylacetyl)-L-alanine isobutyl ester

Procedure

Following General Procedure B′ and using phenylacetyl chloride (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B′ above), the title compound was prepared as a solid having a melting point of 45°-47° 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-76c9ab9a8d084998bf3cff4fa8800431
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262302B1

Reaction notes

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