Ammonium Chloride → HCID 9857659, compound

To a solution of zinc chloride (2.0 g, 0.015 mol) and sodium borohydride (1.1 g, 0.029 mol) in t-butyl methyl ether (80 ml) was added dropwise a solution of (4S,5S)-5-hydroxy-4-isopropyl-5-trifluoromethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester (5.0 g, 0.015 mol) obtained in Example 2 in t-butyl methyl ether (20 ml), and the mixture was stirred at room temperature for 15 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution (80 ml), and the mixture was extracted with ethyl acetate (50 ml). The extract was washed with a saturated brine, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and thereto were added each 25 ml of methanol and water, and potassium carbonate (3.1 g), and the mixture was stirred for one hour. The reaction solvent was evaporated under reduced pressure, and thereto was added water (50 ml). The mixture was extracted three times with ethyl acetate (each 50 ml). The extract was washed with a saturated brine, and the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration and washed with hexane to give the desired compound (3.0 g, yield: 87%).

1. extractionthe mixture was extracted with ethyl acetate (50 ml)
2. washThe extract was washed with a saturated brine
3. dry with materialthe organic layer was dried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. additionwere added each 25 ml of methanol and water, and potassium carbonate (3.1 g)
6. stirringthe mixture was stirred for one hour
7. customThe reaction solvent was evaporated under reduced pressure
8. additionwas added water (50 ml)
9. extractionThe mixture was extracted three times with ethyl acetate (each 50 ml)
10. washThe extract was washed with a saturated brine
11. dry with materialthe organic layer was dried over magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. filtrationThe precipitated crystals were collected by filtration
14. washwashed with hexane

ORD record

ord-2fe373002b734b7aa05ee25e4e355c86

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06646150B1