HCID 86629023, compound → HCID 25218128, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (24c) (0.45 g, 1.1 mmol) and 400 mg of 10 wt.-% of palladium on activated carbon in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 140 mg (39% yield) of the title compound (24) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.97 (s, 3H), 1.12 (s, 3H), 2.01 (s, 3H), 2.04-2.13 (m, 2H), 2.94-3.08 (br. s, 1H), 3.13-2.26 (m, 2H), 3.33-3.48 (m, 2H), 3.83 (s, 3H), 3.97 (d, J=8.8 Hz, 1H), 4.06 (br. s, 1H), 3.97 (d, J=9.6 Hz, 1H), 6.02-6.09 (br. m, 1H) ppm. MS (ESI) m/z: 325.95 (M+H)+, 323.97 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence