Trifluoroacetic acid → HCID 19605015, compound

Participants

Reaction Steps

A 8 ml potion of trifluoroacetic acid was dissolved in 2.46 g of 5-acetoxymethyl-2-(N-t-butoxycarbonylamino)methylthiazole under ice-cooling, and the mixture was then allowed to stand at room temperature for 1 hour. Then, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in 24.6 ml of dichloromethane under ice-cooling. Furthermore, 40 ml of an aqueous saturated sodium bicarbonate solution was added thereto, followed by stirring. To this solution, a 10% aqueous sodium carbonate solution and a mixed acid anhydride solution comprising a mixed solution of 3.7 ml of formic acid and 2.0 ml of acetic anhydride which had been beforehand reacted with each other at 50° C. for 30 minutes were added dropwise under ice-cooling so that the pH of the reaction solution might be within the range of 3.0 to 6.5. Afterward, the organic layer was separated, and the remaining aqueous layer was concentrated under reduced pressure until its amount became half, followed by extraction with chloroform (15 ml×4). The combined organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure to obtain 1.74 g of 5-acetoxymethyl-2-(formylamino)methylthiazole.

Provenance & Evidence