HCID 178435494, compound → HCID 178435492, compound

HRID 1741240Notes

Reaction equation

HRID 1741240 reaction equation
[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[CH:34]([CH3:35])[CH:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH:27](C(OC)=O)[C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45]>N1C(C)=CC=CC=1C>[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[C@@H:34]([CH3:35])[C@H:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH2:27][C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45]

Participants

3

Reactant 1

HCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Procedure

To a solution of methyl pheophorbide-a (25 g, 42.5 mmol) in 2,6-lutidine (1 L) was added distilled water (10 mL, 556 mmol, 13 equiv., 1% v/v) and the mixture was refluxed under argon with stirring. The reaction was monitored by HPLC (hexane-acetone, 90:10-mobile phase, LiChrospherCN-column, detection at 425 and 410 nm). After 100 min. of reflux, the HPLC of reaction aliquots showed 99.7% of completion. The solution was cooled to room temperature after 120 min of reflux and solvent removed under reduced pressure. Hexane (100 mL) was added and the solid was collected by filtration and rinsed with hexane to remove any traces of 2,6-lutidine. The solid was then precipitated from methylene chloride-methanol to give methyl pyropheophorbide-a (20.3 g, 91%).

Workup

  1. distillationdistilled water (10 mL, 556 mmol, 13 equiv., 1% v/v) and the mixture
  2. temperaturewas refluxed under argon
  3. temperatureAfter 100 min. of reflux
  4. customthe HPLC of reaction aliquots
  5. temperatureof reflux
  6. customsolvent removed under reduced pressure
  7. additionHexane (100 mL) was added
  8. filtrationthe solid was collected by filtration
  9. washrinsed with hexane
  10. customto remove any traces of 2,6-lutidine
  11. customThe solid was then precipitated from methylene chloride-methanol

Sources & evidence

ORD record
ord-4ba4fa940c494aa8847f426c32bd1957
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

Loading…