تفاعل #819166

معادلة التفاعل

4-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol

→

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

المذيبات

CHCl3

ظروف التفاعل

المعالجة

1. 1
   غسيلpreparative, 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. 2
   أخرىAfter combination of fractions and evaporation of the solvent in vacuo, one peak (99.8%) with a retention time of 8.078 minutes
3. 3
   أخرىwas isolated as a white solid (200 mg, 100%

الإجراء التجريبي

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]−).

المصدر