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

HRID 428065Notes

Reaction equation

HRID 428065 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 B and using 4-chlorophenylacetic acid (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 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-f176b7c4d69e4c32ad654b1550908ffd
Source dataset
uspto-grants-2001_11
Patent number
US06313152B1

Reaction notes

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