Acetic Acid → HCID 131722297, compound

Participants

Reaction Steps

Acetic acid (0.30 ml) and 1.75 ml of a 1 M tetra-n-butylammonium fluoride/THF solution are added to a solution of 300 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-[5-(allyloxycarbonylaminomethyl)imidazo[5,1-b]thiazol-3-yl]methyl-N-methylaminocarbonyl]pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate in 5.2 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 27.5 hr. 1/15 M phosphate buffer (pH 7.0) (10 ml) is added thereto, and the mixture is extracted twice with 30 ml of ethyl acetate. The combined organic layers are dried over a 1:1 mixture of anhydrous magnesium sulfate and potassium carbonate and filtered, and the solvent is removed under reduced pressure and by filtrate to give a colorless viscous material. The viscous material is successively purified by column chromatography on silica gel (ethyl acetate:methanol=97:3 to 95:5) and on Sephadex LH-20 (chloroform:methanol=1:1) to give 212.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-[5-(allyloxycarbonylaminomethyl)imidazo[5,1-b]thiazol-3-yl]methyl-N-methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate as a colorless amorphous material.

Provenance & Evidence