Ammonium Chloride → HCID 67157743, compound

The compound (950 mg, 2.66 mmol) synthesized in Example 17 (17f) was dissolved in methanol (10 mL) and sodium methoxide (270 μL, 1.30 mmol) was added thereto, followed by stirring of the mixture at room temperature for 15 minutes. After saturated aqueous ammonium chloride solution (50 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with ethyl acetate (50 mL), the organic layer was washed with saturated brine (50 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and saturated aqueous sodium hydrogencarbonate (50 mL) and benzyl oxychloroformate (570 μL, 4.00 mmol) were added thereto at 0° C., followed by stirring of the mixture at 0° C. for 1 hour. The organic layer was washed with saturated brine (50 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1, V/V) to obtain the desired title compound (1.00 g, yield 97%) as a colorless solid.

1. extractionthe mixture was extracted with ethyl acetate (50 mL)
2. washthe organic layer was washed with saturated brine (50 mL)
3. dry with materialdried with anhydrous sodium sulfate
4. distillationby distilling off of the solvent under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
6. customat 0° C.
7. stirringby stirring of the mixture at 0° C. for 1 hour
8. washThe organic layer was washed with saturated brine (50 mL)
9. dry with materialdried with anhydrous sodium sulfate
10. distillationby distilling off of the solvent under reduced pressure
11. customThe residue was purified

ORD record

ord-19a01b3600ec4b8aaf1bc9ec019cd911

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361744B2