反应详情

{(S)-1-benzyloxymethyl-2-[2-oxo-2-(3,4,5-trifluorophenyl)ethoxy]ethyl}carbamic acid t-butyl ester (82.6 g) was diluted with 4 N hydrochloric acid-ethyl acetate solution (500 mL), and the resultant was stirred at room temperature for 12 hours. The solvent was removed under a vacuum, and the resultant was dissolved in methanol (500 mL). 10% palladium on carbon (8.5 g, 50% water content) was added, and under a hydrogen atmosphere, stirring was continued for 22 hours. The catalyst was filtered off on celite, and the filtrate was concentrated under a vacuum. The residue was diluted with methanol (500 mL), and 20% palladium hydroxide on carbon (8 g, 50% water content) was added, and under a hydrogen atmosphere, stirring was continued for 4 hours. The catalyst was filtered off on celite, and the solvent was removed under a vacuum. Ethyl acetate (600 mL) and 1 N sodium hydroxide solution (250 mL) was added, and the organic layer was partitioned. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The residue was suspended in ether (80 mL) and the resultant was filtered, and the title compound (22.34 g) was obtained. The physical property values are as follows.

1. customThe solvent was removed under a vacuum
2. dissolutionthe resultant was dissolved in methanol (500 mL)
3. addition10% palladium on carbon (8.5 g, 50% water content) was added
4. stirringunder a hydrogen atmosphere, stirring
5. waitwas continued for 22 hours
6. filtrationThe catalyst was filtered off on celite
7. concentrationthe filtrate was concentrated under a vacuum
8. additionThe residue was diluted with methanol (500 mL), and 20% palladium hydroxide on carbon (8 g, 50% water content)
9. additionwas added
10. stirringunder a hydrogen atmosphere, stirring
11. waitwas continued for 4 hours
12. filtrationThe catalyst was filtered off on celite
13. customthe solvent was removed under a vacuum
14. additionEthyl acetate (600 mL) and 1 N sodium hydroxide solution (250 mL) was added
15. customthe organic layer was partitioned
16. washThe organic layer was washed with brine
17. dry with materialdried over anhydrous magnesium sulfate
18. filtrationthe resultant was filtered