Water → (1R,5S,6S)-6-((1R)-1-Hydroxyethyl)-2-[(3S,5R)-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylic acid

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (14.3 mg) is added to a solution of 71 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate and 0.08 ml of N-methylaniline in 1.0 ml of dry dichloromethane, and the mixture is stirred in an argon atmosphere at room temperature for 40 min. Distilled water (3 ml) and 5 ml of ethyl acetate are added thereto to remove insolubles, followed by washing twice with 5 ml of ethyl acetate and concentration under reduced pressure. The concentrate is then freeze dried to give a colorless flocculent material. This material is then purified by column chromatography on Cosmosil 40C18-PREP (water:methanol) to give 6.12 mg of the title compound as a colorless flocculent material.

Provenance & Evidence