Triethylamine → 1-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide

Participants

Reaction Steps

To a stirred mixture of 1-[(2S,3R)-2-benzyloxy-5-hydroxy-3-pentyl]imidazole-4-carboxamide (330 mg, 1.09 mmol) and methanesulfonyl chloride (249 mg, 2.18 mmol) in dichloromethane (10 ml) was added dropwise triethylamine (220 mg, 2.18 mmol) at ice-bath temperature. After 1 hour, the reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo to give 1-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide (430 mg, 103%) as an oil. This material was used for the next reaction without further purification.

Provenance & Evidence