Methanol → HCID 54439973, compound

Participants

Reaction Steps

To a mixture of methyl 4-[7-(cyclopentyl acetamido)naphth-1-ylmethyl]-3-methoxybenzoate (660 mg), methanol (23 ml) and tetrahydrofuran (23 ml) was added a solution of lithium hydroxide monohydrate (321 mg) in water (7.7 ml). Nitrogen was bubbled through the mixture for 30 seconds before it was stoppered and stirred for 72 h. The reaction mixture was evaporated and the residue taken up in 75 ml of 1:9 tetrahydrofuran:ethyl acetate and acidified with 3 ml of 6N HCl. The organic layer was washed (water, brine), dried (MgSO4) and evaporated. Recrystallization of the resulting solid from 1:9 methanol:methylene chloride and petroleum ether gave the title compound as a colorless solid (517 mg, 81%); mp 248.0°-250.0° C.

Provenance & Evidence