HCID 86629020, compound → HCID 25207673, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (22b) (0.8 g, 1.8 mmol) and 700 mg palladium (10 wt. % on activated carbon) in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 380 mg (61% yield) of the title compound (22) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.96 (s, 3H), 1.13 (s, 3H), 1.34 (t, J=7.2 Hz, 3H), 1.99 (s, 3H), 2.04-2.12 (m, 2H), 3.12-3.26 (m, 2H), 3.32 (d, J=6.0 Hz, 1H), 3.34-3.47 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 4.03 (d, J=6.0 Hz, 1H), 4.16 (d, J=9.6 Hz, 1H), 4.23-4.26 (m, 2H), 6.00-6.06 (br. m, 1H) ppm. MS (ESI) m/z: 339.95 (M+H)+, 337.94 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence