Dichloromethane → HCID 22876217, compound

Participants

Reaction Steps

To a solution of 1.108 of the above-obtained 5-[(S)-1-(trifluoroacetylamino)ethyl]imidazo[5,1-b]thiazole in 20 ml of methanol was added a solution of 2.70 g of potassium carbonate in 20 ml of water, and the mixture was stirred at room temperature under argon atmosphere for 14 hours. To the reaction solution was added 50 ml of methylene chloride. To this mixture was added with ice-cooling a mixture of 0.50 g of formic acid and 0.25 g of acetic anhydride, which had been heated to 50° C. for 10 minutes and then cooled to room temperature, and the resulting mixture was stirred for an additional 30 minutes. 2.70 g of potassium carbonate was added to this reaction solution to obtain a solution, to which was added again with ice-cooling a mixture of 0.50 g of formic acid and 0.25 g of acetic anhydride, which had been heated to 50° C. for 10 minutes and then cooled to room temperature, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration. The organic layer was separated, and the aqueous layer was extracted with methylene chloride (30 ml×2). The combined organic layers were dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting first with ethyl acetate and then with a 20:1 mixture of ethyl acetate and methanol to give 0.763 g (yield 93%) of the title compound.

Provenance & Evidence