Carbon Dioxide → 1,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[2-(2-hydroxyethyldithio)ethoxy]azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate

Participants

Reaction Steps

A solution of mitomycin A (100 mg or 0.286 mmole) in 4 ml of 2-hydroxyethyldisulphide was stirred at room temperature and under nitrogen for 45 minutes with 240 mg of a 1.6% solution of KOH in 2-hydroxyethyldisulphide. The reaction mixture was decomposed with excess dry ice while immersing the flask into a water bath at room temperature. The reaction mixture was chromatographed on a silica gel column using CHCl3 -acetone 1:1 and the CHCl3 -MeOH 9:1 as solvent systems. The product was further purified by preparative thin layer chromatography on silica gel using CHCl3 -acetone 3:7. Thus, there was obtained 23 mg (44%) of the desired product, having a melting point of 87°-95° C. (decomposition) and providing the following analysis:

Provenance & Evidence