反应详情

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol (5 g) was dissolved in methanol (35 mL) and tetrahydrofuran (25 mL) at room temperature. A solution of LiOH hydrate (192 mg) in water (10 mL) was added dropwise to the mixture for 30 minutes at 20-24° C. After the mixture was stirred for 19 hours at room temperature, the solvent was evaporated in vacuo. The residue was partitioned to ethyl acetate (50 mL) and water (25 mL), stirred for 15 minutes, then the layers were separated. The organic layer was washed with water. The organic layer was dried over Na2SO4, filtered using activated carbon pre-coated filter and evaporated. The resulting residue was dissolved in ethyl acetate (11.1 mL) at 40° C., water (241 mL) was added to the mixture at the same temperature. n-Heptane (5.6 mL) was added to the mixture at 40° C., then the mixture was seeded with a slight amount of (1S)-1,5-anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol at same temperature. After stirred for 1 hour at 35° C., n-heptane (2.6 mL) was added slowly to the mixture. The resulting mixture was cooled. The precipitate was filtered and washed with ethyl acetate/n-heptane, then dried to give hemihydrate of (1S)-1,5-anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol (2.93 g) as white crystals.

1. customat room temperature
2. customthe solvent was evaporated in vacuo
3. customThe residue was partitioned to ethyl acetate (50 mL) and water (25 mL)
4. stirringstirred for 15 minutes
5. customthe layers were separated
6. washThe organic layer was washed with water
7. dry with materialThe organic layer was dried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. dissolutionThe resulting residue was dissolved in ethyl acetate (11.1 mL) at 40° C.
11. additionwater (241 mL) was added to the mixture at the same temperature
12. additionn-Heptane (5.6 mL) was added to the mixture at 40° C.
13. stirringAfter stirred for 1 hour at 35° C.
14. additionn-heptane (2.6 mL) was added slowly to the mixture
15. temperatureThe resulting mixture was cooled
16. filtrationThe precipitate was filtered
17. washwashed with ethyl acetate/n-heptane
18. customdried