Hydrochloric Acid → HCID 25225744, compound

Participants

Reaction Steps

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (methylethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (40c) (13.0 g, 24.4 mmol), 3.2 g of 10 wt.-% of palladium on activated carbon in 40 mL of methanol (MeOH), and 0.2 mL of one molar (1.0 M) hydrochloric acid (HCl) was stirred overnight under a hydrogen atmosphere. Upon the completion of reaction and following aqueous work-up, 10.0 g (93% yield) of the title compound (40) was obtained as a colorless, viscous oil. RT=12.46 min and 14.22 min. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.89-0.91 (2s, 3H), 0.93-0.95 (2s, 3H), 1.21-1.24 (m, 6H), 1.45-1.47 (2d, J=5.2, 5.2 Hz, 3H), 1.78-1.83 (m, 5H), 3.10-3.15 (m, 2H), 3.30-3.33 (m, 2H), 3.89-3.93 (m, 2H), 4.05-4.08 (2d, J=9.2, 9.6 Hz, 1H), 4.73-4.82 (m, 1H), 5.78-5.85 (2d, J=6.0, 6.0 Hz, 1H), 6.65-6.71 (m, 1H), 7.89-7.92 (br. m, 1H) ppm. MS (ESI) m/z: 442.08 (M+H)+, 464.02 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence