Hydrazine hydrate (1:1) → HCID 14301775, compound

Participants

Reaction Steps

0.6 ml of hydrazine monohydrate was added to a solution of 815 mg of t-butyl α-{6(R)-[1(S)-t-butoxycarbonyl-5-phthalimidopentylamino]-5-oxo-2(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate (prepared as described in Example 1) dissolved in a mixture of 3 ml of methylene chloride and 3 ml of ethanol, whilst ice-cooling, and the mixture was stirred at room temperature for 4 days. At the end of this time, the precipitate which appeared in the reaction mixture was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue was mixed with ethyl acetate and the precipitated material was filtered off. The ethyl acetate filtrate was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure to remove the solvent. The residue was subjected to column chromatography through silica gel using mixtures of ethyl acetate and methanol in the proportions 10:1 and 4:1 by volume as the eluent to yield 302 mg of the title compound as syrup.

Provenance & Evidence