HCID 178435494, compound → HCID 178435492, compound

HRID 1741242Notes

Reaction equation

HRID 1741242 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(C)=CC(C)=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

3

Reactant 1

HCID 178435494HCID 178435494, compound

Product 1

HCID 178435492HCID 178435492, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in 2,4,6-collidine (25 mL, distilled) was added distilled water (1 mL, 56 mmol, 327 equiv., 4% v/v) 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 90 min, the reaction was shown to have reached 99.5% completion by HPLC peak area. The solution was cooled to room temperature and solvent removed under reduced pressure. Hexane (10 mL) was added and the precipitated porphyrin was collected by filtration and rinsed with hexane to give methyl pyropheophorbide-a (65 mg, 72%).

Workup

  1. distillationdistilled water (1 mL, 56 mmol, 327 equiv., 4% v/v) and the mixture
  2. temperaturewas refluxed under argon
  3. customsolvent removed under reduced pressure
  4. additionHexane (10 mL) was added
  5. filtrationthe precipitated porphyrin was collected by filtration
  6. washrinsed with hexane

Sources & evidence

ORD record
ord-2d832dd921dd4a0695f2384fa153447c
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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