Water → methyl (1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-aminophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Step 5 (200 mg, 0.43 mmol) dissolved in ethanol (3.7 mL) and water (0.57 mL) was added iron (72.4 mg, 1.29 mmol). Saturated aqueous ammonium chloride (0.57 mL) was added and heated the mixture to 70° C. The reaction was stirred for 8 h at 70° C., then cooled to room temperature, diluted with ethyl acetate, and filtered. The filter cake was washed with 1:1 ethanol:ethyl acetate, and then the filtrate was washed with 1:1 water:saturated aqueous sodium bicarbonate. The filtrate was extracted with ethyl acetate (3×) and the combined organic layers were washed with brine, and then dried over sodium sulfate, filtered, and concentrated to give methyl(1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-aminophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate (186.5 mg, 0.43 mmol, 100% yield) as a yellow foam. MS ESI: [M+H]+ m/z 433.2.

Provenance & Evidence