Ammonia chloride → HCID 59759352, compound

{2-[(2-tert-Butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid (127 g) synthesized in Example 3 was added to 1M-borane/tetrahydrofuran complex (800 mL) under ice-cooling, and the mixture was stirred at room temperature for 8 hr. The reaction mixture was ice-cooled, methanol (400 mL) was added dropwise. After warming to room temperature, the mixture was stirred for 1 hr. Then, saturated aqueous ammonia chloride (300 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (110 g) as a slightly yellow oil.

1. temperaturecooling
2. temperaturecooled
3. temperatureAfter warming to room temperature
4. stirringthe mixture was stirred for 1 hr
5. stirringthe mixture was stirred at room temperature for 1 hr
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. additionpoured into water
8. extractionthe mixture was extracted with ethyl acetate
9. washThe organic layer was washed with saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

ORD record

ord-e1ed7ae70f204b58a797bf3289ec15c0

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026370B2