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0 °C

A solution of Intermediate 141 (0.3769 g, 0.3505 mmol) in MeOH (7 mL) was degassed by bubbling N2 through the solution for approximately 10 minutes. The solution was cooled to 0° C. and Pd/C (0.3850 g of 10 wt %) was added slowly. The reaction flask was purged and filled with H2 3× before stirring under H2 (1 atm, balloon). The reaction mixture was warmed to room temperature and reaction progress was monitored by LC-MS. After 72 h, the reaction mixture was filtered through a pad of Celite. The filter cake was washed with 1:1 DCM/MeOH. The filtrate was concentrated and the residue was dissolved in 3:1 MeOH/EtOAc. The solution was degassed and cooled as described above; Pd/C (0.311 g of 10 wt %) was added and the mixture was placed under H2 atmosphere as described above. Reaction progress was monitored by LC-MS. After 24 h, the reaction mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient elution 1:19 to 1:3 MeOH/DCM) to yield the title compound (0.155 g, 45%) as a yellow solid. ES/MS calcd for C53H61N6O9SSi+ 985.4. Found m/z=985.5 (M+H)+.

1. customby bubbling N2 through the solution for approximately 10 minutes
2. additionPd/C (0.3850 g of 10 wt %) was added slowly
3. customThe reaction flask was purged
4. additionfilled with H2 3×
5. temperatureThe reaction mixture was warmed to room temperature
6. customreaction progress
7. filtrationthe reaction mixture was filtered through a pad of Celite
8. washThe filter cake was washed with 1:1 DCM/MeOH
9. concentrationThe filtrate was concentrated
10. dissolutionthe residue was dissolved in 3:1 MeOH/EtOAc
11. customThe solution was degassed
12. temperaturecooled
13. additionPd/C (0.311 g of 10 wt %) was added
14. customReaction progress
15. waitAfter 24 h
16. filtrationthe reaction mixture was filtered through a pad of Celite
17. concentrationthe filtrate was concentrated under reduced pressure
18. customThe residue was purified by column chromatography on silica gel (gradient elution 1:19 to 1:3 MeOH/DCM)