HCID 178435494, compound → HCID 178435492, compound

HRID 1741241Notes

Reaction equation

HRID 1741241 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=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 99%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Procedure

To a solution of methyl pheophorbide-a (100 g, 165 mmol) in 2,6-lutidine (4 L) was added distilled water (40 mL, 2.22 mol, 13 equiv., 1% 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). The HPLC of reaction aliquot after 90 min showed 99.5% of completion. The solution was cooled to room temperature after 120 min of reflux and solvent removed under reduced pressure with water bath at 45-50° C. Hexane (120 mL) was added and the solid was collected by filtration and rinsed with hexane to remove any traces of 2,6-lutidine. The solid was vacuum dried to give methyl pyropheophorbide-a (89.6 g, 99%).

Workup

  1. distillationdistilled water (40 mL, 2.22 mol, 13 equiv., 1% v/v) and the mixture
  2. temperaturewas refluxed under argon
  3. customThe HPLC of reaction aliquot after 90 min
  4. temperatureof reflux
  5. customsolvent removed under reduced pressure with water bath at 45-50° C
  6. additionHexane (120 mL) was added
  7. filtrationthe solid was collected by filtration
  8. washrinsed with hexane
  9. customto remove any traces of 2,6-lutidine
  10. customdried

Sources & evidence

ORD record
ord-6498e6227aba483d8a4c059ec146f145
Source dataset
uspto-grants-1999_10
Patent number
US05973141

Reaction notes

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