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

HRID 2180805Notes

Reaction equation

HRID 2180805 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-591296460c584c64993a46193313245c
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

Loading…