Hydrochloric Acid → HCID 25225740, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of (cyclohexylcarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (44c) (0.79 g, 1.4 mmol), 0.4 g of 10 wt.-% of palladium on activated carbon in 20 mL of methanol (MeOH), and 30 μL of one molar (1.0 M) of hydrochloric acid (HCl) was stirred overnight under a hydrogen atmosphere. Upon the completion of reaction and following aqueous work-up, 0.62 g (94% yield) of the title compound (44) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.92-0.94 (2s, 3H), 0.97-0.98 (2s, 3H), 1.20-1.42 (br. m, 5H), 1.46-1.48 (2d, J=5.6, 5.6 Hz, 3H), 1.55-1.62 (br. m, 1H), 1.66-1.70 (br. m, 2H), 1.80-1.87 (m, 7H), 2.33-2.40 (m, 1H), 3.14-3.19 (m, 2H), 3.34-3.37 (m, 2H), 3.92-3.96 (m, 2H), 4.09-4.12 (2d, J=9.2, 9.6 Hz, 1H), 5.50-6.87 (2d, J=5.2, 5.6 Hz, 1H), 6.81-6.87 (m, 1H), 7.95-7.98 (br. m, 1H) ppm. MS (ESI) m/z: 466.10 (M+H)+, 488.07 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence