Anisole → HCID 86745935, compound

Participants

Reaction Steps

An ice-cooled solution of 3-trifluoromethyl-2-(4-methoxybenzylthio)-N-[2-(4-methoxyphenyl)-1-(S)-(methylaminocarbonyl)ethyl]-α-(2-methylpropyl)phenylpropanamide (D13) (308 mg, 0.5 mmol) and anisole (0.1 ml) in trifluoroacetic acid (5 ml) was treated with mercuric acetate (160 mg, 0.5 mmol). After 15 min the solvent was evaporated and the residue was azeotroped dry with toluene. The residual oil was triturated with ether to give a white solid, which was separated and washed with a little ether. The solid was dissolved in dry DMF (3 ml) and the solution was purged with nitrogen. Hydrogen sulphide gas was bubbled through the solution for 3 min. The resulting black suspension was purged with nitrogen for 30 min, then the solvent was evaporated in vacuo. Column chromatography (10 g silica) eluting with ethyl acetate and trituration of the product with pentane gave the title compound as a 1:1 mixture of diastereoisomers (88 mg, 35%), mp 88°-102° C.

Provenance & Evidence