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

HRID 133354Notes

Reaction equation

HRID 133354 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 BB and using 3,4-dichlorophenylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid haying a melting point of 811-83° 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.

Workup

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

Sources & evidence

ORD record
ord-80d4b5a788e64df1b4a3942bf1ceafaa
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

Loading…