3,4-Dichlorophenylacetic acid → N-[(3,4dichlorophenyl)acetyl]-L-alanine iso-butyl ester

HRID 1533534Notes

Reaction equation

HRID 1533534 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH2:14]([O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH2:21])[CH:15]([CH3:17])[CH3:16]>>[CH2:14]([O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH:21][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 798743,4-Dichlorophenylacetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 15481766N-[(3,4dichlorophenyl)acetyl]-L-alanine iso-butyl ester

Procedure

Following General Procedure B′ and using 3,4-dichlorophenylacetic 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 81°-83° 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-4a253943ab8b459d8c4ead9aa614a90f
Source dataset
uspto-grants-2001_03
Patent number
US06207710B1

Reaction notes

Loading…