Sodium Cyanide → HCID 90384415, compound

Temperature

50 °C

To the compound (98.8 mg, 0.400 mmol) of Step 1 of Example 21, NBS (78.3 mg, 0.440 mmol), and a catalytic amount of BPO, carbon tetrachloride (4 mL) was added, and heated under reflux overnight. The resultant was returned to room temperature, and the solvent was distilled away under reduced pressure. The resulting residue was diluted with dichloromethane, washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was dissolved in acetonitrile (2 mL), and sodium cyanide (39.2 mg, 0.800 mmol) and water (0.2 mL) were added thereto, and stirred at 50° C. for 30 minutes. To the reaction solution, a 1 N sodium hydroxide aqueous solution was added. After concentrated under reduced pressure, the resultant was diluted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography to thus obtain the title compound.

1. temperatureheated
2. temperatureunder reflux overnight
3. customwas returned to room temperature
4. distillationthe solvent was distilled away under reduced pressure
5. additionThe resulting residue was diluted with dichloromethane
6. washwashed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationThe solvent was distilled away under reduced pressure
9. dissolutionThe resulting residue was dissolved in acetonitrile (2 mL)
10. concentrationAfter concentrated under reduced pressure
11. additionthe resultant was diluted with ethyl acetate
12. washwashed with water and saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. distillationThe solvent was distilled away under reduced pressure
15. customThe resulting residue was purified by silica gel chromatography

ORD record

ord-30aa3b5df36c42cdae6140a67198d31e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290487B2