4-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol → 4-{[(6S)-3-chloro-6-methylphenanthridin-5(6H)-yl]carbonyl}phenol

HRID 731984Notes

Reaction equation

HRID 731984 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:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=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]=[CH:20][C:21]([OH:24])=[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 116603034-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol

Product 1

HCID 116244604-{[(6S)-3-chloro-6-methylphenanthridin-5(6H)-yl]carbonyl}phenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The enantiomers of 4-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol (400 mg, 1.14 mmol) were separated by automated, on-column solvent change, preparative, normal phase, chiral chromatography on a Chiralpak AD (20 mm×250 mm) column eluting with 20% ethanol in hexane at a flow rate of 12 mL/min with. After combination of fractions and evaporation of the solvent in vacuo, one peak (99.8%) with a retention time of 8.078 minutes was isolated as a white solid (200 mg, 100% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 200 mg). mp 273.7-276° C.; [α]D25=+393° (c=0.010 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.73 Hz, 3 H) 5.67 (q, J=6.73 Hz, 1 H) 6.71 (d, J=8.79 Hz, 2 H) 6.79 (d, J=2.07 Hz, 1 H) 7.17 (d, J=8.54 Hz, 2 H) 7.26 (dd, J=8.41, 2.20 Hz, 1 H) 7.41 (m, 3 H) 7.98 (m, 2 H) 10.04 (s, 1 H); MS (ESI) m/z 350/352 ([M+H]+); MS (ESI) m/z 348/350 ([M−H]−).

Workup

  1. washpreparative, normal phase, chiral chromatography on a Chiralpak AD (20 mm×250 mm) column eluting with 20% ethanol in hexane at a flow rate of 12 mL/min with
  2. customAfter combination of fractions and evaporation of the solvent in vacuo, one peak (99.8%) with a retention time of 8.078 minutes
  3. customwas isolated as a white solid (200 mg, 100%

Sources & evidence

ORD record
ord-d650e00053b6411db2f0cadc333c87cb
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

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