Hydrogen Sulfide → HCID 14696317, compound

Participants

Reaction Steps

1.010 g of (2R)-N-(α,α-dimethylbenzyl)-2-benzoylamino-3-(p-methoxybenzylthio)propionamide [prepared as described in step (a) above] was dissolved in 10 ml of trifluoroacetic acid. To this solution was added 1.0 ml of anisole and, whilst ice-cooling, this was followed by the addition of 793 mg of mercuric acetate under a nitrogen stream, and then the mixture was stirred. After stirring for 1.5 hours, the solvent was distilled off at room temperature. Diethyl ether was added to the residue and the material which separated out was filtered off. This material obtained by filtration (the mercuric salt) was dissolved in 50 ml of dimethylformamide, and, whilst ice-cooling, hydrogen sulfide gas was passed through this solution. After 1.5 hours, the mercuric sulfide which separated out was filtered off with Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure at room temperature to give 702 mg of the title compound as crystals melting at 169°-173° C.

Provenance & Evidence