p-Anisoyl chloride → HCID 10767748, compound

Participants

Reaction Conditions

Reaction Steps

Compound C was suspended in THF (350 ml) and powdered sodium carbonate (18.5 g) was added. The mixture was cooled to -5° C. and a solution of anisoyl chloride (11.9 g) in THF (50 ml) was added with stirring. The reaction mixture was stirred an additional 2 hours at 0° C. and then allowed to rise to ambient temperature. The reaction mixture was filtered and the filtrate acidified with 1M hydrochloric acid solution (20 ml) and washed with water. The aqueous layer was extracted with twice with diethyl ether and the combined organic layers washed with 50% saturated sodium bicarbonate solution, brine and dried. Solvent was removed by evaporation to give a colourless foam. The foam was triturated with diethyl ether and the resulting solid was collected by filtration and dried under vacuum at 40° C. for 3 hours to give (S)-1-[(S)-2-(4-methoxybenzamido)-3-methylbutyryl]-N-[(S)-2-methyl-1-((R)-2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide as a white solid, m.p. 168°-170° C.; NMR (300 MHz, d6 -DMSO): 0.82-1.05 (m, 12H), 1.65-2.05 (3m, 5H), 2.05-2.25 (m, 1H), 3.60 (m, 1H), 3.82 (s, 3H+t, 1H), 3.93 (m, 1H), 4.12 (m, 1H), 4.45 (m, 2H), 6.45 (d, 1H), 6.98 (d, 2H), 7.65 (d, 1H), 7.90 (d, 2H), 8.35 (d, 1H).

Provenance & Evidence