Glycine ethyl ester, hydrochloride → N-(3-Nitrophenylacetyl)-L-alaninylglycine Ethyl Ester

HRID 1016921Notes

Reaction equation

HRID 1016921 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([OH:18])=O)[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[CH3:21]>>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH:25][C:16](=[O:18])[C@H:14]([CH3:15])[NH:13][C:11](=[O:12])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:21]

Participants

3

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 9819161N-(3-Nitrophenylacetyl)-L-alaninylglycine Ethyl Ester

Procedure

Following General Procedure C and using N-(3-nitrophenylacetyl)-L-alanine (prepared from 3-nitrophenylacetic acid (Aldrich) and L-alanine ethyl ester hydrochloride (Sigma) using General Procedure C, followed by hydrolysis using General Procedure AF) and glycine ethyl ester hydrochloride (Sigma), the title compound was prepared as a solid (mp=164-165 ° C.). The product was purified by silica gel chromatography using EtOAc as the eluent, followed by recrystallization from EtOAc.

Workup

  1. customThe product was purified by silica gel chromatography
  2. customfollowed by recrystallization from EtOAc

Sources & evidence

ORD record
ord-f34edf96b81a444dabcb05b98cfb5020
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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