Dimethyl Sulfoxide → HCID 86595162, compound

Participants

Reaction Steps

Under N2, a cold (−75° C.) solution of oxalyl chloride (285 mg, 2.24 mmol) in CH2Cl2 (10 ml) was treated with DMSO (0.215 ml, 3.03 mmol) and stirred for 10 min. A solution of ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-3-pentyl]imidazole-4-carboxylate (400 mg, 1.12 mmol) in CH2Cl2 (5 ml) was slowly added, the resulting mixture was stirred for 50 min at −75 to −45° C. and finally treated with triethylamine (0.59 ml). The reaction mixture was allowed to warm to 0° C., hydrolyzed with water (10 ml) and extracted with CH2Cl2 (20 ml×2). The combined organic layers were dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel (13 g) chromatography eluting with chloroform/methanol (100:1) to give ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-oxo-3-pentyl]imidazole-4-carboxylate (370 mg, 93%) as a colorless syrup.

Provenance & Evidence