HCID 86628913, compound → HCID 25225547, compound

Participants

Reaction Steps

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (cyclohexyloxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (43c) (0.19 g, 0.34 mmol) and 0.13 g of 10 wt.-% of palladium on activated carbon in 10 mL of methanol (MeOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 0.13 g (80% yield) of the title compound (43) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.89-0.90 (2s, 3H), 0.93-0.94 (2s, 3H), 1.31-1.47 (br. m, 9H), 1.60-1.68 (br. m, 2H), 1.78-1.83 (br. m, 7H), 3.10-3.15 (m, 2H), 3.28-3.35 (m, 2H), 3.89-3.92 (m, 2H), 4.05-4.08 (2d, J=9.2, 9.6 Hz, 1H), 4.52-4.58 (m, 1H), 5.78-5.85 (2d, J=5.6, 5.6 Hz, 1H), 6.66-6.72 (m, 1H), 7.89-7.92 (br. m, 1H) ppm. MS (ESI) m/z: 482.07 (M+H)+, 503.83 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence