Ammonia → HCID 67490740, compound

A solution of (1S,6S)-1-tert-butoxycarbonylamino-8-benzyloxycarbonyl-8-azabicyclo[4.3.0]non-3-ene (400 mg, 1.07 mmol) in tetrahydrofuran (5.35 mL) was bubbled with ammonia gas under cooling with dry ice-methanol for 10 minutes to add 30 to 40 mL of liquid ammonia to the solution. Sodium (128 mg, 5.34 mmol) was added, and the mixture was stirred for 10 minutes. A saturated ammonium chloride solution (15 drops) was added at room temperature, and the mixture was stirred at room temperature to evaporate ammonia. A 1 mol/L sodium hydroxide solution (15.0 mL) was added, followed by extraction with chloroform (30 mL×2). The aqueous layer was concentrated under reduced pressure. A 1 mol/L sodium hydroxide solution (5.0 mL) was added, followed by extraction with the lower layer of chloroform/methanol/water=7/3/1 (35 mL×2). The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure to give 136 mg of the title compound as a white amorphous.

1. stirringthe mixture was stirred at room temperature
2. customto evaporate ammonia
3. additionA 1 mol/L sodium hydroxide solution (15.0 mL) was added
4. extractionfollowed by extraction with chloroform (30 mL×2)
5. concentrationThe aqueous layer was concentrated under reduced pressure
6. additionA 1 mol/L sodium hydroxide solution (5.0 mL) was added
7. extractionfollowed by extraction with the lower layer of chloroform/methanol/water=7/3/1 (35 mL×2)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationThen, the filtrate was concentrated under reduced pressure

ORD record

ord-382b1f74accd4670a458c46c599e3e61

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2