Hydrochloric Acid → HCID 66681631, compound

Temperature

0 °C

Ethyl (2-bromo-1,3-thiazol-4-yl)(oxo)acetate (3.07 g, 11.6 mmol) synthesized in Example (9a) was dissolved in methanol (100 mL), and cooled to 0° C. Sodium borohydride (1.32 g, 34.9 mmol) was added in small portions, and stirring was carried out at 0° C. for 1.5 hours, followed by stirring at room temperature for further 2 hours. Dilute hydrochloric acid (1M, 100 mL) was added, and the solution was separated with ethyl acetate (200 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-80%) to afford the desired compound (1.10 g, yield 42%) as a yellow oil.

1. stirringby stirring at room temperature for further 2 hours
2. customthe solution was separated with ethyl acetate (200 mL)
3. washThe organic layer was washed with saturated brine
4. dry with materialsubsequently dried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe resulting residue was purified
7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-80%)

ORD record

ord-7083e63be4554a8dbebbb60d71eafa85

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2