HCID 25218255, compound → HCID 25218381, compound

Participants

Reaction Steps

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of phenylmethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-2-hydroxy-3,3-dimethylbutanoate (31) (40 mg, 0.1 mmol) and 30 mg of 10 wt-% palladium on activated carbon in 2 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After filtration through a 0.2 μM nylon syringe filter and evaporation of the solvents, 6.7 mg (23% yield) of the title compound (33) was obtained as a pale-yellow, viscous oil. 1H NMR (400 MHz, DMSO-d6): δ=0.90 (s, 3H), 0.91 (s, 3H), 1.80 (s, 3H), 1.76-1.85 (m, 2H), 3.09-3.16 (m, 2H), 3.28-3.35 (m, 2H, superimposed with residual water), 3.76-3.82 (br. m, 1H), 3.94 (d, J=8.8 Hz, 1H), 4.07 (d, J=8.8 Hz, 1H), 7.90 (br. t, J=5.2 Hz, 1H), 12.59 (br. s, 1H) ppm. MS (ESI) m/z: 312.0 (M+H)+, 334.0 (M+Na)+, 310.1 (M−H)−. The analytical data was consistent with the proposed structure.

Provenance & Evidence