Water → HCID 178435492, compound

HRID 1741237Notes

Reaction equation

HRID 1741237 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.CCCCCC.CC(C)=O>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

5

Reactant 3

HCID 962Water2×HCID 21880519Acetone hexaneHCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in pyridine (25 mL) was added distilled water (48 μL, 2.7 mmol, 16 equiv.) 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). The HPLC of the reaction aliquots after 2 h and 20 min showed 87% completion (by peak area). After 2 h and 40 min of reflux, more distilled water (32 L, 1.8 mmol, 11 equiv.) was added and reflux continued. An HPLC of reaction aliquot at 5 h and 40 min showed 99.5% completion (by peak area). The solution was cooled to room temperature and solvent removed under reduced pressure. The residue was crystallized from methylene chloride-methanol to give methyl pyropheophorbide-a (50 mg, 56%).

Workup

  1. temperaturethe mixture was refluxed under argon
  2. customThe HPLC of the reaction aliquots after 2 h
  3. custom20 min
  4. temperature40 min of reflux
  5. additionwas added
  6. temperaturereflux
  7. customAn HPLC of reaction aliquot at 5 h
  8. custom40 min
  9. customsolvent removed under reduced pressure
  10. customThe residue was crystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-45da70b1283c4b51a6a92a1cab8c3615
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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