L-Serine, ethyl ester, hydrochloride (1:1) → N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-serine Ethyl Ester

HRID 322745Notes

Reaction equation

HRID 322745 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:28])[C@H:24]([CH2:26][OH:27])[NH2:25])[CH3:21]>CO.C(Cl)(Cl)Cl>[CH2:20]([O:22][C:23](=[O:28])[C@H:24]([CH2:26][OH:27])[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

4

Reactant 2

HCID 2724185L-Serine, ethyl ester, hydrochloride (1:1)HCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 22895019N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-serine Ethyl Ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

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 L-serine ethyl ester hydrochloride (Sigma), the title compound was prepared as a solid (mp=179-181° C.). The reaction was monitored by tlc (Rf=0.2 in 5% MeOH/CHCl3) and the product was purified by silica gel chromatography using 5% MeOH/CHCl3 as the eluent.

Workup

  1. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a3440fb8807342abb51739494b27ac87
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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