Hydrochloric Acid → HCID 70220637, compound

Participants

Reaction Steps

Concentrated hydrochloric acid (1.3 ml) is added to a solution of 1.37 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-methylthioimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine in 15 ml of acetonitrile under ice cooling, and the mixture is stirred for 30 min. The reaction mixture is neutralized with a saturated sodium hydrogencarbonate solution, and ethyl acetate is added, followed by extraction three times. The extract is washed three times with semi-saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation to give 1.03 g of (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-(5-methylthioimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine. This compound is dissolved in 18 ml of THF, 1.53 g of triphenylphosphine and 0.92 ml of diethyl azodicarboxylate are added thereto at −17° C., and the mixture is stirred for 30 min. Further, 0.7 ml of thiobenzoic acid is added thereto, and the mixture is stirred at about −20° C. for 40 min. The solvent is removed by evaporation, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 1.06 g of the title compound as a yellow oil.

Provenance & Evidence