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

HRID 2271130Notes

Reaction equation

HRID 2271130 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.

Workup

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

Sources & evidence

ORD record
ord-04df4b4994e849ab87725743a61f06b5
Source dataset
uspto-grants-2001_12
Patent number
US06333351B1

Reaction notes

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