3-Nitrophenylacetic acid → N-[(3-nitrophenyl)acetyl]-alanine iso-butyl ester

HRID 478827Notes

Reaction equation

HRID 478827 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH2:15]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[CH:16]([CH3:18])[CH3:17]>>[CH2:15]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH:22][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:16]([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 158763-Nitrophenylacetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 54157293N-[(3-nitrophenyl)acetyl]-alanine iso-butyl ester

Procedure

Following General Procedure H above and using 3-nitrophenylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by recrystallization from butyl chloride. NMR data was as follows:

Workup

  1. customThe reaction was monitored by tlc on silica gel and purification
  2. customwas by recrystallization from butyl chloride

Sources & evidence

ORD record
ord-5c2d56646619431b8dacdf642c59c8d6
Source dataset
uspto-grants-2003_11
Patent number
US06642261B2

Reaction notes

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