Methanol → HCID 25225745, compound

Participants

Reaction Steps

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of [2-(phenylmethoxy)acetyloxy]ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (45a) (0.10 g, 0.17 mmol) and 0.1 g of 10 wt.-% of palladium on activated carbon in 6 mL of a mixture of methanol (MeOH) and ethyl acetate (EtOAc) was stirred overnight under a hydrogen atmosphere. After work-up and further purification by mass-guided preparative HPLC, 51 mg (73% yield) of the title compound (45) was obtained as a colorless, viscous oil after lyophilization of the solvents. 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.02-1.05 (2s, 3H), 1.10-1.13 (2s, 3H), 1.60 (t, J=5.2 Hz, 3H), 2.01 (s, 3H), 2.05-2.12 (m, 2H), 2.84-3.03 (br. m, 1H), 3.14-3.26 (m, 2H), 3.34-3.46 (m, 2H), 3.97-4.16 (m, 3H), 4.22 (s, 2H), 5.56-5.96 (br. m, 1H), 7.00-7.08 (m, 1H) ppm. MS (ESI) m/z: 414.02 (M+H)+, 435.96 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence