(R)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide
Reaction equation
[O:1]=[C:2]1C=C(C(O)=O)C=[CH:4][N:3]1[C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12].BrC1C=C(C=CC=1)O[C@H](C1[CH:44]=[CH:43][C:29]([C:30]([NH:32][CH2:33][C:34]2[C:35]([OH:42])=[N:36][C:37]([CH3:41])=[CH:38][C:39]=2[CH3:40])=[O:31])=[CH:28][CH:27]=1)C>>[CH3:40][C:39]1[CH:38]=[C:37]([CH3:41])[NH:36][C:35](=[O:42])[C:34]=1[CH2:33][NH:32][C:30]([C:29]1[C:43]([CH3:44])=[CH:4][N:3]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:2](=[O:1])[C:28]=1[CH3:27])=[O:31]Participants
3
Procedure
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide (70 mg) were separated by SFC (Condition: Column: AS (250*30 mm, 5 um), eluent: CO2:EtOH:NH3.H2O=78:22:0.1, flow rate: 50 ml/min, column temperature: 38° C., wavelength: 220 nm) to give 15.6 mg and 14.8 mg of two enantiomers. The LCMS and HNMR of two enantiomers were the same as the racemic compound. Although the separated enantiomers were not optically characterized, for convenience sake the (R) enantiomer was designated Compound I-201 and the (S) enantiomer was designated Compound I-202.
Workup
- customN-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3,5-dimethyl-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide (70 mg) were separated by SFC (Condition: Column: AS (250*30 mm, 5 um), eluent: CO2:EtOH:NH3.H2O=78:22:0.1, flow rate: 50 ml/min, column temperature: 38° C., wavelength: 220 nm)
- customto give 15.6 mg and 14.8 mg of two enantiomers
Sources & evidence
- ORD record
- ord-566815f1b2fc46a2b05c6a0049202c89
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206128B2
Reaction notes
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