Methyl 3-phenyl-DL-alaninate hydrochloride → N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl ester

HRID 861593

Reaktionsgleichung

Reaktionsgleichung von HRID 861593
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](N1C=CN=C1)=[S:12].Cl.[CH3:19][O:20][C:21](=[O:31])[CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH2:23]>CN(C)C=O>[CH3:19][O:20][C:21](=[O:31])[CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:23][C:11]([NH:10][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[S:12]

Komponenten

4

Edukt 2

HCID 3084017Methyl 3-phenyl-DL-alaninate hydrochlorideHCID 19703709N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

Produkt 1

HCID 19703398N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl esterAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-[(2-benzothiazolyl) thiocarbamoyl] imidazole (1.30 g, 5.0 mmol) and DL-phenylalanine methyl ester hydrochloride (1.08 g, 5.0 mmol) in N,N-dimethylformamide (50 mL) was heated at 90° C. for 3 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, recrystallized from ethyl ether-hexanes to provide 1.31 g (70%) of the titled product:

Aufarbeitung

  1. customsolvent removed under reduced pressure
  2. customrecrystallized from ethyl ether-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6ebd263c517a4d39a1c05a4f3e9c7d8b
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714503

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