HCID 178435494, compound → HCID 178435492, compound

HRID 1741239Notes

Reaction equation

HRID 1741239 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=CC=CC=1>[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 1049PyridineSolvent

Procedure

To a solution of methyl pheophorbide-a (25 g, 42.5 mmol) in pyridine (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). An HPLC of the reaction aliquot after 9 hours of reflux showed 99% completion (by peak area). The solution was cooled to room temperature after 10 hours of reflux and solvent removed under reduced pressure. The residue was precipitated first from methylene chloride-hexane and then methylene chloride/methanol. The solid collected was then purified on a silica gel column, eluted with 2% acetone/methylene chloride. The desired fraction was collected and 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. customAn HPLC of the reaction aliquot after 9 hours
  4. temperatureof reflux
  5. temperatureof reflux
  6. customsolvent removed under reduced pressure
  7. customThe residue was precipitated first from methylene chloride-hexane
  8. customThe solid collected
  9. customwas then purified on a silica gel column
  10. washeluted with 2% acetone/methylene chloride
  11. customThe desired fraction was collected
  12. customprecipitated from methylene chloride/methanol

Sources & evidence

ORD record
ord-50c8e432c2f94e84a6134798a1e8ca61
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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