HCID 178435494, compound → HCID 178435492, compound

HRID 1741248Notes

Reaction equation

HRID 1741248 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, compound2×

Product 1

HCID 178435492HCID 178435492, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl pheophorbide-a (2.0 g, 3.3 mmol) in pyridine (80 mL) was added distilled water (0.8 mL) and the mixture was refluxed under argon with stirring. The reaction was monitored by HPLC (Waters instrument, hexane-acetone, 90:10-mobile phase; LiChrospher CN-column; detection at 410 nm). The HPLC of reaction aliquot after 8.5 h of reflux showed <1% (peak area) of starting methyl pheophorbide-a. The reaction was stopped, cooled to room temperature and solvent removed under reduced pressure. The residue was precipitated from methylene chloride-hexane to give methyl pyropheophorbide-a (1.8 g, 100%).

Workup

  1. distillationdistilled water (0.8 mL)
  2. temperaturethe mixture was refluxed under argon
  3. customThe HPLC of reaction aliquot after 8.5 h
  4. temperatureof reflux
  5. customsolvent removed under reduced pressure
  6. customThe residue was precipitated from methylene chloride-hexane

Sources & evidence

ORD record
ord-0f01d9d3e8fa4cf0a5b170ae98a6db83
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

Loading…