Ethyl Acetate → HCID 18714160, compound

Participants

Reaction Steps

A solution of the 8-(4-(4-(2-di(ethylsulfanyl)methyl-(2S)-tetrahydro-1H-1-pyrrolylcarbonyl)-2-methoxy-5-aminophenoxy)butoxy)-7-methoxy-5,11-dioxo-(2R,11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-2-yl acetate of formula V (744 mg, 1 mmol), HgCl2 (794 mg, 2.93 mmol) and HgO (687 mg, 3.18 mmol) in CH3CN/H2O (3:1, 15 ml) was stirred at room temperature for 12 h until TLC (EtOAc) indicated complete loss of starting material. Then the organic layer was evaporated in a vacuum and the residue was diluted with EtOAc. To this, saturated NaHCO3 was added slowly at room temperature and the mixture was filtered through celite and washed with ethylacetate. The filtrate was evaporated in a vacuum to obtain crude 7-methoxy-8-(4-(7-methoxy-5-oxo-(11aR)-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8-yloxy)butoxy)-5,11-dioxo-(2R,11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-2-yl acetate of formula VI, which was further purified by column chromatography on silica gel by eluting first with ethylacetate to remove traces of mercuric salts and then with MeOH:CHCl3 (2:8).

Provenance & Evidence