Hydrogen Peroxide → (3S,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydro furan-3-carboxylic acid

Temperature

5 °C

Sodium hydroxide solution (prepared from 17.7 g of sodium hydroxide and 390 ml of water) was added to a pre-cooled solution of hydrogen peroxide (30 ml), water (65 ml) and tetrahydrofuran (390 ml) at 0-10° C., followed by a solution of (R)-3-((3S,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-carbonyl)-4-phenyloxazolidin-2-one compound of formula-6 (130 g) in tetrahydrofuran (390 ml) at 0-10° C. and the reaction mixture was stirred for 30 minutes at 0-10° C. Further temperature of the reaction mixture was raised to 25-30° C. and then stirred for 2 hours at 25-30° C. After completion of the reaction, the reaction mixture was quenched with 10% sodium sulphite solution and the reaction mixture was washed with toluene. The pH of aqueous layer was adjusted to 10.5 using 50% HCl and then washed with dichloromethane. Further pH of aqueous layer was again adjusted to 4.5 using 50% HCl. The aqueous layer was extracted with methyl tertiary butyl ether and distilled off the solvent from methyl tert.butyl ether layer and then co-distilled with cyclohexane. Cyclohexane (190 ml) was added to the obtained compound and stirred for 2 hours at 25-30° C. Filtered the solid, washed with cyclohexane and then dried to get title compound. Yield: 65 g; MR: 80-87° C.

1. temperatureFurther temperature of the reaction mixture was raised to 25-30° C.
2. stirringstirred for 2 hours at 25-30° C
3. customAfter completion of the reaction
4. customthe reaction mixture was quenched with 10% sodium sulphite solution
5. washthe reaction mixture was washed with toluene
6. washwashed with dichloromethane
7. extractionThe aqueous layer was extracted with methyl tertiary butyl ether
8. distillationdistilled off the solvent from methyl tert.butyl ether layer
9. additionCyclohexane (190 ml) was added to the obtained compound
10. stirringstirred for 2 hours at 25-30° C
11. filtrationFiltered the solid
12. washwashed with cyclohexane
13. customdried

ORD record

ord-f695a42b49a248d98f8bd7b72366a54f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102664B2