Water → HCID 178435492, compound

HRID 1741247Notes

Reaction equation

HRID 1741247 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].O>>[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 2

HCID 962WaterHCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 81.8%

Procedure

Methyl pheophorbide-a (23 g, 37.9 mmol) was added to distilled 2,4,6-collidine (700 mL, Aldrich) and the mixture was refluxed under argon with stirring. After 7 hours of reflux, TLC showed the majority of methyl pheophorbide-a remained. Distilled water (2.5 mL, 139 mmol, 3.7 equiv.) was added and the solution was continued to reflux under argon. After 45 min. the reaction was complete by TLC. The solution was cooled to room temperature and solvent removed under reduced pressure. The residue was precipitated from methylene chloride/methanol, then purified on a silica gel column. The desired fraction was collected, solvent was evaporated off, and the fraction was precipitated from methylene chloride/methanol to give methyl pyropheophorbide-a (17 g, 81%).

Workup

  1. distillationto distilled 2,4,6-collidine (700 mL, Aldrich)
  2. temperaturethe mixture was refluxed under argon
  3. temperatureAfter 7 hours of reflux
  4. temperatureto reflux under argon
  5. customsolvent removed under reduced pressure
  6. customThe residue was precipitated from methylene chloride/methanol
  7. custompurified on a silica gel column
  8. customThe desired fraction was collected
  9. customsolvent was evaporated off
  10. customthe fraction was precipitated from methylene chloride/methanol

Sources & evidence

ORD record
ord-9abdafafcb434af3a97fe643095cdcb3
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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