(methylethoxycarbonyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate → HCID 86628891, compound

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Reaction Steps

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (methylethoxycarbonyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (27c) (16 mg, 0.03 mmol) and 20 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, 11 mg (83% yield) of the title compound (27) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=1.01 (s, 3H), 1.13 (s, 3H), 1.33-1.35 (m, 6H), 2.00 (s, 3H), 2.07-2.11 (m, 2H), 3.13-3.26 (m, 2H), 3.35-3.45 (m, 2H), 3.97 (d, J=9.2 Hz, 1H), 4.12 (s, 1H), 4.16 (d, J=9.6 Hz, 1H), 4.94 (sept., J=6.4 Hz, 1H), 5.79 (d, J=5.6 Hz, 1H), 5.81-5.89 (br. m, 1H), 5.91 (d, J=5.6 Hz, 1H), ppm. MS (ESI) m/z: 428.04 (M+H)+, 450.02 (M+Na)+. The analytical data was consistent with the proposed structure.

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