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

HRID 636194Notes

Reaction equation

HRID 636194 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-12e3b91134d14a6794a568a1252c9773
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Reaction notes

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