HCID 86628895, compound → HCID 25225741, compound

Participants

Reaction Steps

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (2-phenylacetyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (28c) (60 mg, 0.11 mmol) and 60 mg of 10 wt.-% of palladium on activated carbon in 2 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 10 mg (20% yield) of the title compound (28) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.91 (s, 3H), 1.00 (s, 3H), 1.98 (s, 3H), 2.03-2.10 (m, 2H), 3.10-3.23 (m, 2H), 3.26 (br., 1H), 3.32-3.45 (m, 2H), 3.70 (s, 2H), 3.90 (d, J=9.6 Hz, 1H), 4.07 (s, 1H), 4.10 (d, J=9.2 Hz, 1H), 5.79 (d, J=5.6 Hz, 1H), 5.85 (br. m, 1H), 5.93 (d, J=5.6 Hz, 1H) 7.26-7.35 (m, 5H) ppm. MS (ESI) m/z: 460.05 (M+H)+, 481.99 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence