Water → HCID 178435492, compound

HRID 1741236Notes

Reaction equation

HRID 1741236 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.[Na+].[Cl-].CCCCCC.CC(C)=O>CN(C=O)C.CC(C)=O.C(Cl)Cl>[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

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 21880519Acetone hexaneHCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in DMF (15 mL) was added distilled water (18 L, 1.0 mmol, 6 equiv.) and NaCl (10 mg, 0.18 mmol, 1 equiv.). 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 40 min the reaction was shown to have reached 99.6% completion by HPLC peak area and a faint baseline spot on TLC (5% acetone/methylene chloride). The solution was cooled to room temperature after 60 min of reflux and solvent removed under reduced pressure. The residue was precipitated from methylene chloride-methanol to give methyl pyropheophorbide-a (60 mg, 67%).

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-d8defbb66ed34396afcfe6578a7205ac
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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