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

HRID 861592

Reaction equation

HRID 861592 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](N1C=CN=C1)=[S:8].Cl.[CH3:15][O:16][C:17](=[O:27])[CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19]>CN(C)C=O>[CH3:15][O:16][C:17](=[O:27])[CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:19][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[S:8]

Participants

4

Reactant 2

HCID 3084017Methyl 3-phenyl-DL-alaninate hydrochlorideHCID 10750950N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 19704073N-[(2-thiazolylamino)thioxomethyl]-DL-phenylalanine methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-thiazolyl) thiocarbamoyl] imidazole (4.21 g, 20.0 mmol) and DL-phenylalanine methyl ester hydrochloride (4.31 g, 20.0 mmol) in N,N-dimethylformamide (150 mL) was heated at 90° C. for 3 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, recrystallized from ether-hexanes to provide 3.26 g (51%) of the titled product:

Workup

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

Sources & evidence

ORD record
ord-62ce2b04828544049f96dfe862f60b8e
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Linked notes

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