HCID 86629041, compound → HCID 25218254, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of 2-methylpropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (30c) (0.43 g, 0.94 mmol) and 400 mg of 10 wt-% palladium on activated carbon in 10 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC and lyophilization of the solvents, 200 mg (58% yield) of the title compound (30) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.96-1.00 (m, 9H), 1.16 (s, 3H), 1.96-2.05 (m, 4H), 2.05-2.14 (m, 2H), 3.13-3.26 (m, 2H), 3.27 (d, J=6.4 Hz, 1H), 3.33-3.49 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 3.98 (d, J=6.4 Hz, 1H), 3.99-4.03 (m, 1H), 4.03-4.07 (m, 1H), 4.18 (d, J=8.8 Hz, 1H), 5.88-5.94 (br. m, 1H) ppm. MS (ESI) m/z: 368.16 (M+H)+, 366.19 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence