Water → HCID 178435492, compound

HRID 1741238Notes

Reaction equation

HRID 1741238 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(C)=CC=CC=1C>[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 962WaterHCID 21880519Acetone hexaneHCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Procedure

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in 2,6-lutidine (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 reaction aliquot after 30 min showed 100% 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 (78 mg, 87%).

Workup

  1. temperaturethe mixture was refluxed under argon
  2. customThe HPLC of reaction aliquot after 30 min
  3. customsolvent removed under reduced pressure
  4. customThe residue was crystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-9ab350ee6e8342189773d8e3b23fa214
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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