Methanol → HCID 18700427, compound

Temperature

50 °C

A solution of 170 g (4.25 mol) sodium hydroxide in 250 mL of water is added to a stirred solution of 84 g (210 mmol) 1-(4-[5-(4-fluoro-phenyl)-4-(2,2,2-trifluoro-ethoxymethyl)-oxazol-2-yl]-piperidin-1-ethanone, prepared as in Part D, in 1L of methanol. The mixture is stirred at 50° C. for 8 hours, cooled to 20° C., and stirred for an additional 12 hrs. The methanol is removed from the reaction mixture under reduced pressure, and the residue is diluted with 1 L water. The mixture is extracted with methylene chloride (3×300 mL). The layers are separated and 50 g of sodium chloride is added to the aqueous phase. The aqueous phase is extracted with methylene chloride (3×300 mL). The organic phases are combined, dried with anhydrous magnesium sulfate, filtered, then concentrated under reduced pressure. The residue is dissolved in 200 mL of ethyl acetate and 600 mL of saturated sodium bicarbonate solution is added and the mixture is stirred at room temperature for 12 hours. The solid is filtered and washed three times with 200 mL of water, and with ether (3×50 mL). The product is dried under reduced pressure at 40° C. to yield the title compound.

1. temperaturecooled to 20° C.
2. stirringstirred for an additional 12 hrs
3. customThe methanol is removed from the reaction mixture under reduced pressure
4. additionthe residue is diluted with 1 L water
5. extractionThe mixture is extracted with methylene chloride (3×300 mL)
6. customThe layers are separated
7. addition50 g of sodium chloride is added to the aqueous phase
8. extractionThe aqueous phase is extracted with methylene chloride (3×300 mL)
9. dry with materialdried with anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. dissolutionThe residue is dissolved in 200 mL of ethyl acetate
13. addition600 mL of saturated sodium bicarbonate solution is added
14. stirringthe mixture is stirred at room temperature for 12 hours
15. filtrationThe solid is filtered
16. washwashed three times with 200 mL of water
17. customThe product is dried under reduced pressure at 40° C.

ORD record

ord-01e6c77012174ccb9198dbd0985983cf

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090825