Water → (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide

A mixture of (S)-2-amino-3-benzyloxy-1-propanol (5.0 g) and triethylamine (7.9 mL) was dissolved in tetrahydrofuran (40 mL), methanesulfonyl chloride (4.4 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (10 mL), sodium chloride (3.2 g) was added, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. A mixture of the obtained residue and 1,10-phenanthroline (28 mg) was dissolved in tetrahydrofuran (80 mL), diisopropylamine (3.9 mL) was added at −70° C., and n-butyllithium (38 mL) was further added. The reaction mixture was heated to room temperature, and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (4.49 g).

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washthe organic layer was washed with saturated brine
4. customthe solvent was evaporated
5. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (10 mL)
6. additionsodium chloride (3.2 g) was added
7. stirringthe mixture was stirred at 80° C. for 5 hr
8. temperatureThe reaction mixture was cooled
9. additionwater was added
10. extractionthe mixture was extracted with ethyl acetate
11. washThe organic layer was washed with saturated brine
12. customthe solvent was evaporated
13. additionA mixture of the obtained residue and 1,10-phenanthroline (28 mg)
14. dissolutionwas dissolved in tetrahydrofuran (80 mL)
15. additiondiisopropylamine (3.9 mL) was added at −70° C.
16. additionn-butyllithium (38 mL) was further added
17. temperatureThe reaction mixture was heated to room temperature
18. stirringstirred overnight
19. additionWater was added to the reaction mixture
20. extractionthe mixture was extracted with ethyl acetate
21. washthe organic layer was washed with saturated brine
22. customthe solvent was evaporated
23. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

ORD record

ord-cc3f00c01f2a419ca8bc1f71620fef1e

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816079B2