Carbon Dioxide → N-[(4R)-2-amino-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-6'-yl]-5-chloropyridine-2-carboxamide

Participants

Reaction Steps

N-(2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl)-5-chloro pyridine-2-carboxamide (352 mg, 0.821 mmol) was subjected to chromatography using supercritical CO2 (supercritical CO2/[EtOH with 0.1% diethylamine]=60:40) on Chiralcel OD-H column (10×250 mm) eluting at a flow rate 10 mL/minute (40° C. column temperature). After concentration of collected fractions of the first peak (retention time=5.23 minutes) at reduced pressure, recrystallization of the residue with EtOH/water (1:1) provided a hydrate of N-[(4R)-2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-chloropyridine-2-carboxamide (153 mg, 44%) as a crystal. After concentration of collected fractions of the second peak (retention time=8.16 minutes) at reduced pressure, recrystallization of the residue with EtOH/water (1:1) provided a hydrate of N-[(4S)-2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-chloropyridine-2-carboxamide (152 mg) as a crystal.

Provenance & Evidence