Diphosgene → HCID 58615504, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[(S)-2-((R)-2-amino-2-phenyl-acetylamino)-3-phenyl-propionylamino]-thiazole-4-carboxylic acid methyl ester (0.795 g, 1.82 mmol) and diisopropylethylamine (1.10 mL, 6.2 mmol) in tetrahydrofuran (20 mL) was added to a solution of diphosgene (0.151 μL, 1.27 mmol) in a mixture of toluene (20 mL) and tetrahydrofuran (20 mL) over 10 minute at 0° C. The mixture was stirred at 0° C. for 20 minute then diluted with ethyl acetate. The mixture was washed with water, brine and dried over sodium sulfate. Evaporation of the solvents and purification of the residue by chromatography over silica gel gradient eluted between 0.2 and 1.2% v/v methanol in dichloromethane followed by recrystallization of the isolated product from acetonitrile gave 2-[(S)-2-((R)-2,5-dioxo-4-phenyl-imidazolidin-1-yl)-3-phenyl-propionylamino]-thiazole-4-carboxylic acid methyl ester as a white crystalline solid (166 mg, 20%).

Provenance & Evidence