Ammonia → HCID 67491225, compound

Participants

Reaction Steps

[(1S,5R)-1-tert-Butoxycarbonylamino-3-azabicyclo[3.3.0]oct-7-en-3-yl]carboxylic acid benzyl ester (85.0 mg, 0.24 mmol) was dissolved in tetrahydrofuran (20 mL). After bubbling with liquid ammonia (20 mL) at −78° C., sodium (17.1 mg, 0.71 mmol) was added, and the mixture was stirred for one hour. A saturated ammonium chloride solution (6 drops) were added, and then ammonia was vaporized in an ice water bath. A 1N sodium hydroxide solution was added, followed by extraction with chloroform twice. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure to give 52.9 mg of the title compound as a colorless solid.

Provenance & Evidence