Methyl 3-phenyl-DL-alaninate hydrochloride → N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1111844

Reaktionsgleichung

Reaktionsgleichung von HRID 1111844
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24](O)=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:28][O:29][C:30](=[O:40])[CH:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:32]>CN(C)C=O>[CH3:28][O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:32][C:24](=[O:25])[C@H:12]([CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Komponenten

4

Edukt 2

HCID 3084017Methyl 3-phenyl-DL-alaninate hydrochlorideHCID 53769026N-carbobenzoxy-beta-benzyl-L-aspartic acid

Produkt 1

HCID 14876780N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl esterAusbeute 45,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The process of Example 51 was repeated except that 357 mg (1.00 mmol) of N-benzyloxycarbonyl-(β-benzyl)-L-aspartic acid and 431 mg (2.00 mmol) of D,L-phenylalanine methyl ester hydrochloride were reacted. As a result, a 238 mg amount (yield of 45.8%) of N-benzyloxycarbonyl-(β-benzyl)-L-aspartyl-L-phenylalanine methyl ester having an [α]D20 = -13.2 (C=1.0 dimethylformamide) was obtained.

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-a821198fce544eb7a337eaa9152cb47f
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04119493

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