Water → HCID 178435492, compound

HRID 1741235Notes

Reaction equation

HRID 1741235 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>CN(C=O)C>[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 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in DMF (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). After 60 min the reaction was shown to have reached 99.6% completion by HPLC peak area. The solution was cooled to room temperature after 100 min of reflux and solvent removed under reduced pressure. The residue was precipitated from methylene chloride-methanol to give methyl pyropheophorbide-a (50 mg, 56%).

Workup

  1. temperaturethe mixture was refluxed under argon
  2. temperatureof reflux
  3. customsolvent removed under reduced pressure
  4. customThe residue was precipitated from methylene chloride-methanol

Sources & evidence

ORD record
ord-d617dff570d14752b60c9f3666e85ad9
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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