Ammonia → HCID 19973071, compound

Participants

Reaction Steps

In 5 ml of ethanol was dissolved 1.0 g of ethyl 4-chloro-2,2-difluoro-3-hydroxy-3-phenylbutyrate. To the resulting solution was added 0.98 ml of a concentrated aqueous ammonia. The solution was subjected to reaction at 25°-30° C. for 3 hours. The solvent was removed by distillation under reduced pressure. To the residue obtained were added 20 ml of ethyl acetate and 20 ml of water. The resulting solution was adjusted to pH 1.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 10 ml of N,N-dimethylformamide. To the solution were added 0.5 g of 1,2,4-triazole and 1.0 g of anhydrous potassium carbonate. The resulting mixture was subjected to reaction at 70° C. for 10 hours. Then, the solvent was removed by distillation under reduced pressure. To the residue obtained were added 20 ml of ethyl acetate and 20 ml of water. The resulting solution was adjusted to pH 1.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant:chloroform/methanol=50/1) to obtain 0.30 g of 2,2-difluoro-3-hydroxy-3-phenyl-4-(1H-1,2,4-triazol-1yl)butanamide.

Provenance & Evidence