反应详情

A solution of 1.26 g (3.8 mmol) 2-3 in 40 mL MeOH was evacuated under reduced pressure and purged with N2 three times before adding a portion of palladium hydroxide on carbon. After purging three more times with N2, the atmosphere was replaced with H2 and the reaction was stirred under a balloon of H2 for 2 h. The reaction was filtered through a pad of celite by rinsing with EtOAc and MeOH, and the filtrate was concentrated to provide a colorless oil. This material was dissolved in 3 mL of DMF and to it was added 683 mg of 2-4 (3.6 mmol; prepared in an analogous fashion to 1-5, see example 1-C), 668 mg (4.3 mmol) 1-hydroxybenzotriazole hydrate, 1.5 mL (10.8 mmol) triethylamine and 831 mg (4.3 mmol) EDC and the reaction was stirred overnight at 60° C. The reaction was partitioned between EtOAc and 10% aqueous citric acid, the layers were separated, and the organic was washed with water, brine, dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide 2-5 as a white solid. Data for 2-5: LC/MS: rt=2.36 min; m/z (M+H)=412.3 found; 412.2 required.

1. custompurged with N2 three times
2. additionbefore adding a portion of palladium hydroxide on carbon
3. customAfter purging three more times with N2
4. filtrationThe reaction was filtered through a pad of celite
5. washby rinsing with EtOAc and MeOH
6. concentrationthe filtrate was concentrated
7. customto provide a colorless oil
8. customprepared in an analogous fashion to 1-5
9. stirringthe reaction was stirred overnight at 60° C
10. customThe reaction was partitioned between EtOAc and 10% aqueous citric acid
11. customthe layers were separated
12. washthe organic was washed with water, brine
13. dry with materialdried over Na2SO4
14. concentrationconcentrated by rotary evaporation
15. customThe residue was purified by column chromatography on silica gel (EtOAc/hexanes)