Carbon Dioxide → HCID 72548948, compound

HRID 873771Notes

Reaction equation

[NH2:1][C:2]1[O:3][CH2:4][C:5]2([N:31]=1)[C:14]1([CH2:17][O:16][CH2:15]1)[C:13]([CH3:19])([CH3:18])[O:12][C:11]1[C:6]2=[CH:7][C:8]([NH:20][C:21]([C:23]2[CH:28]=[N:27][C:26]([O:29][CH3:30])=[CH:25][N:24]=2)=[O:22])=[CH:9][CH:10]=1.C(=O)=O>>[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:31]=1)[C:14]1([CH2:15][O:16][CH2:17]1)[C:13]([CH3:18])([CH3:19])[O:12][C:11]1[C:6]2=[CH:7][C:8]([NH:20][C:21]([C:23]2[CH:28]=[N:27][C:26]([O:29][CH3:30])=[CH:25][N:24]=2)=[O:22])=[CH:9][CH:10]=1

Participants

Reactant 2

HCID 280Carbon Dioxide

HCID 86724320HCID 86724320, compound

Product 1

HCID 72548948HCID 72548948, compoundYield 35%

Procedure

N-[2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-methoxypyrazine-2-carboxamide (100 mg, 0.235 mmol) was chromatographed using supercritical CO2 (supercritical CO2/EtOH=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=5.25 minutes) under reduced pressure, trituration of the residue with EtOAc/hexane provided N-[(4S)-2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-methoxypyrazine-2-carboxamide (35 mg). After concentration of collected fractions of the second peak (retention time=8.08 minutes) under reduced pressure, trituration of the residue with EtOAc/hexane provided N-[(4R)-2-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-6′-yl]-5-methoxypyrazine-2-carboxamide (35 mg).

Workup

washeluting at a flow rate 10 mL/minute (40° C. column temperature)

Sources & evidence

ORD record: ord-5d0c1ee2d55c4d37a0375b39b60b6ef4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975415B2

Reaction notes

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