HCID 131729100, compound → HCID 25218127, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of ethyl (2R/S)-4-{[3-(acetylamino)propyl]sulfonyloxy}-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (23c) (0.26 g, 0.56 mmol) and 140 mg of 10 wt.-% of palladium on activated carbon in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC and lyophilization of the solvents, 130 mg (68% yield) of the title compound (23) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.97 (s, 3H), 1.14 (s, 3H), 1.35 (t, J=6.8 Hz, 3H), 2.01 (s, 3H), 2.06-2.13 (m, 2H), 3.13-2.26 (m, 2H), 3.33-3.46 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 4.04 (s, 1H), 4.17 (d, J=9.2 Hz, 1H), 4.26-4.35 (m, 2H), 5.92 (br. m, 1H) ppm. MS (ESI) m/z: 340.04 (M+H)+, 338.01 (M−H)−. The analytical data was consistent with the proposed structure and the data for the enantiopure compound (22).

Provenance & Evidence