HCID 11688866, compound → HCID 11624459, compound

HRID 731979Notes

Reaction equation

HRID 731979 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:25])[N:13]([C:16]([C:18]4[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=4)=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C@@H:12]([CH3:25])[N:13]([C:16]([C:18]4[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=4)=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

3

Reactant 1

HCID 11688866HCID 11688866, compound

Product 1

HCID 11624459HCID 11624459, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The enantiomers of 3-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol (367 mg, 1.05 mmol) were separated by automated, preparative, normal phase, chiral chromatography on a Chiralpak AD (20 mm×250 mm) column eluting with 100% ethanol at a flow rate of 10 mL/min. After combination of fractions and evaporation of the solvent in vacuo, one peak with a retention time of 3.801 minutes was isolated as a white solid (144 mg, 79% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 183.5 mg). [α]D25=−398° (c=0.010 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.73 Hz, 3 H) 5.65 (d, J=6.47 Hz, 1 H) 6.70 (d, J=7.50 Hz, 1 H) 6.73 (s, 1 H) 6.84 (ddd, J=8.15, 2.46, 0.78 Hz, 1 H) 6.92 (s, 1H) 7.17 (t, J=7.89 Hz, 1 H) 7.28 (dd, J=8.41, 2.20 Hz, 1 H) 7.39 (m, 2 H) 7.45 (m, 1H) 7.98 (d, J=8.54 Hz, 2 H) 9.68 (s, 1 H); MS (ESI) m/z 350/352 ([M+H]+); MS (ESI) m/z 348/350 ([M−H]−); HRMS: calcd for C21H16ClNO2, 349.0870 (M), 350.09424 ([M+H]+); found (ESI+), 350.09353.

Workup

  1. washeluting with 100% ethanol at a flow rate of 10 mL/min
  2. customAfter combination of fractions and evaporation of the solvent in vacuo, one peak with a retention time of 3.801 minutes
  3. customwas isolated as a white solid (144 mg, 79%

Sources & evidence

ORD record
ord-c041e09d2e0149e1816cd7af1ca190fc
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

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