Acetic Acid → HCID 14349717, compound

Participants

Reaction Steps

A mixture of 1.16 g of (6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[[thioxo[[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester, 660 mg of zinc dust, 0.25 ml of glacial acetic acid, 2 ml of 1M aqueous potassium dihydrogen phosphate and 10 ml of tetrahydrofuran was stirred for 1 hour and then filtered. The filtrate was subjected to flash chromatography, eluting with ethyl acetate:petroleum ether in a 1:1 to 1:2 gradient, giving 340 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[(aminothioxomethyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester and 30 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[[[[(2,2-dichloroethoxy)carbonyl]amino]thioxomethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester.

Provenance & Evidence