isopropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate → HCID 25218129, compound

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Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of isopropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (25c) (0.20 g, 0.45 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 after lyophilization of the solvents, 100 mg (63% yield) of the title compound (25) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.95 (s, 3H), 1.13 (s, 3H), 1.32 (d, J=6.0 Hz, 3H), 1.34 (d, J=6.4 Hz, 3H), 1.99 (s, 3H), 2.02-2.16 (m, 2H), 3.12-3.26 (m, 2H), 3.29 (br. d, J=6.0 Hz, 1H), 3.32-3.47 (m, 2H), 3.95 (d, J=9.6 Hz, 1H), 3.99 (br. d, J=4.8 Hz, 1H), 4.17 (d, J=9.2 Hz, 1H), 5.14 (septet, J=6.4 Hz, 1H), 6.00-6.06 (br. m, 1H) ppm. MS (ESI) m/z: 354.13 (M+H)+, 352.16 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence