HCID 86629038, compound → HCID 25218253, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of 3-methylbutyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (29c) (0.20 g, 0.42 mmol) and 200 mg of 10 wt-% of palladium on activated carbon in 10 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 160 mg (quant. yield) of the title compound (29) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.943 (d, J=6.8 Hz, 3H), 0.946 (d, J=6.8 Hz, 3H), 0.947 (s, 3H), 1.13 (s, 3H), 1.55-1.62 (m, 2H), 1.63-1.76 (m, 1H), 1.99 (s, 3H), 2.02-2.13 (m, 2H), 3.12-3.26 (m, 3H), 3.31-3.46 (m, 2H), 3.95 (d, J=9.6 Hz, 1H), 4.03 (s, 1H), 4.17 (d, J=9.2 Hz, 1H), 4.24 (t, J=6.8 Hz, 2H), 6.06-6.12 (br. m, 1H) ppm. MS (ESI) m/z: 382.00 (M+H)+, 380.04 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence