(4-Chlorophenyl)acetic acid → N-[(4chlorophenyl)acetyl]-L-alanine Iso-butyl Ester

HRID 133353Notes

Reaction equation

HRID 133353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[CH2:13]([O:17][C:18](=[O:22])[C@H:19]([CH3:21])[NH2:20])[CH:14]([CH3:16])[CH3:15]>>[CH2:13]([O:17][C:18](=[O:22])[C@H:19]([CH3:21])[NH:20][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:14]([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 15481765N-[(4chlorophenyl)acetyl]-L-alanine Iso-butyl Ester

Procedure

Following General Procedure BB and using 4-chlorophenylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid having a melting point of 111°-113° 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.

Workup

  1. customThe reaction was monitored by tlc on silica gel and purification
  2. extractionwas by extraction with Et2O

Sources & evidence

ORD record
ord-923170d5407d40a594e42f59cca54466
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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