HCID 178435494, compound → HCID 178435492, compound

HRID 1836085Notes

Reaction equation

HRID 1836085 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 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl pheophorbide-a (5) (1.3 g, 2.09 mmol) was dissolved in 100 mL of pyridine and stirred at reflux for 8 hours under nitrogen in the dark. Pyridine was removed by evaporation and the residue was recrystallized from dichloromethane/methanol to give 1.08 g (92%) of methyl pyropheophorbide-a (39). UV/vis Omax (H)(CH2Cl2): 410 (112500), 509 (11400), 537 (9800), 611 (8500), 669 (47000) nm.

Workup

  1. temperatureat reflux for 8 hours under nitrogen in the dark
  2. customPyridine was removed by evaporation
  3. customthe residue was recrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-3ded260388a545eea535f5f1627f6586
Source dataset
uspto-grants-2004_08
Patent number
US06777402B2

Reaction notes

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