Hydrochloric Acid → HCID 86686873, compound

Participants

Reaction Steps

To a solution of (4-aza-1-azoniabicyclo[2.2.2]oct-1-ylsulfonyl)(tert-butoxycarbonyl)azanide-1,4-diazabicyclo[2.2.2]octane (1:1) hydrochloride (43.4 g, 98.6 mmol) in acetonitrile (30 mL), in a 500 mL reactor, was added (1S,2S,4R)-4-(6-((1R,2S)-5-chloro-2-methoxy-2,3-dihydro-1H-inden-1-ylamino)pyrimidin-4-yloxy)-2-(hydroxymethyl)cyclopentanol (27) (10 g, 24.6 mmol) in N-methylpyrrolidinone (60 mL). The resultant thick slurry was stirred at ambient temperature for 3 hours. Upon reaction completion, water (66.6 mL) was added slowly at ambient temperature. To the resulting mixture, ethyl acetate (66.7 mL) was added. The aqueous layer was extract three times with ethyl acetate (3×66.6 mL). The combined organic layers were washed once with water (66.7 mL) and once with saturated sodium chloride in water (66.7 mL). The combined organic layers were dried over magnesium sulfate (3 g), filtered and concentrated. This product was taken on to the next step without further purification.

Provenance & Evidence