L-Tyrosine ethyl ester → N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-tyrosine Ethyl Ester

HRID 322740Notes

Reaction equation

HRID 322740 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].[CH2:19]([O:21][C:22](=[O:33])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH2:24])[CH3:20]>CCOC(C)=O>[CH2:19]([O:21][C:22](=[O:33])[C@H:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[NH:24][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)[CH3:20]

Participants

4

Reactant 2

HCID 70364L-Tyrosine ethyl esterHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 9824664N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-tyrosine Ethyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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-tyrosine ethyl ester (Sigma), the title compound was prepared as a solid (mp=117-119° C.). The reaction was monitored by tlc (Rf=0.5 in EtOAc) and the product was purified by silica gel chromatography using EtOAc as the eluent.

Workup

  1. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ac70b82d67894345991235c6e4011ef0
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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