Methanol → HCID 846127, compound

Participants

Reaction Steps

L-phenylalanyl methyl ester hydrochloride was converted into the corresponding free base by shaking with a sodium bicarbonate solution in ether and heated to 100° for 2.5 hours in glacial acetic acid with acetonylacetone. Thereafter, the solvent was evaporated and the residue was filtered with toluene over silica gel, to obtain methyl (S)-α-benzyl-2,5-dimethylpyrrole-1-acetate, MS: 258 (M+H)+. The ester so obtained was allowed to stand at room temperature for 1.5 hours with 1N sodium hydroxide solution in a 9:1 mixture of methanol and water. After extracting the aqueous solution with ether and washing the organic phase, there was obtained (S)-α-benzyl-2,5-dimethylpyrrole-1-acetic acid, MS: 244 (M+H)+, which was used directly in the next step.

Provenance & Evidence