Methyl 2-amino-3-(3-hydroxyphenyl)propanoate → Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-2-amino3-(3-hydroxyphenyl)propionate

HRID 1016922Notes

Reaction equation

HRID 1016922 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].[NH2:19][CH:20]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=1)[C:21]([O:23][CH3:24])=[O:22]>CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:19][CH:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])=[O:18])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 22386100Methyl 2-amino-3-(3-hydroxyphenyl)propanoateHCID 53788870N-(3-Nitrophenylacetyl)-L-alanine

Product 1

HCID 10159696Methyl N-[N-(3-nitrophenylacetyl)-L-alaninyl]-2-amino3-(3-hydroxyphenyl)propionate

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 methyl 2-amino-3-(3-hydroxyphenyl)propionate (prepared from 2-amino-3-(3-hydroxyphenyl)propionate (Biosynth AG, Switzerland) and methanol using General Procedure H), the title compound was prepared as a solid (mp=155-159° C.). The reaction was monitored by tlc (Rf=0.4 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-b0ea99b2aa774235beee9648c259e52e
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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