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

HRID 322739

Reaktionsgleichung

Reaktionsgleichung von HRID 322739
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customthe product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a0e03da8ca464209b970eef01cadd5be
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211235B1

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