Hydrochloric Acid → HCID 71093016, compound

A solution of 2-methyl-propane-2-sulfinic acid [(S)-2,2-difluoro-1-fluoromethyl-1-(2-fluoro-phenyl)-3-hydroxy-propyl]-amide (intermediate F4.1) (145.5 mg, 426 μmol) in methanol (2.5 ml) was cooled to 0° C. and treated with hydrochloric acid (4 M in dioxane; (533 μl, 2.13 mmol). The solution was left to warm to room temperature and stirred for 1 hour. After removal of the solvent at reduced pressure the solid residue was dissolved in water (5 ml), then extracted with ethyl acetate (2×10 ml). The organic layers were extracted with water (5 ml), thereafter the combined aqueous layers treated with a solution of sodium carbonate (2 M) to adjust the pH to 9-10. Extraction with ethyl acetate (3×35 ml), combination of the organic layers and evaporation at reduced pressure after drying over sodium sulphate yielded the crude (S)-3-amino-2,2,4-trifluoro-3-(2-fluoro-phenyl)-butan-1-ol (78 mg, 78% yield) as a colorless oil. Evaporation of the first 2 ethyl acetate layers followed by the treatment with a solution of sodium carbonate and proceeding as described above yielded another fraction (22 mg) of product. MS (ISN): m/z=238.1 [M+H]+.

1. waitThe solution was left
2. customAfter removal of the solvent at reduced pressure the solid residue
3. dissolutionwas dissolved in water (5 ml)
4. extractionextracted with ethyl acetate (2×10 ml)
5. extractionThe organic layers were extracted with water (5 ml)
6. additionthe combined aqueous layers treated with a solution of sodium carbonate (2 M)
7. extractionExtraction
8. customwith ethyl acetate (3×35 ml), combination of the organic layers and evaporation at reduced pressure
9. dry with materialafter drying over sodium sulphate

ORD record

ord-29507457c0c54b0e8326552ab3da4388

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987255B2