Sulfuric Acid → HCID 178435494, compound

HRID 891828Notes

Reaction equation

HRID 891828 reaction equation
CC1C(CCC(O)=O)=C(CC2NC(/C=C3/C(C=C)=C(C)C(N/3)=O)=C(C)C=2CCC(O)=O)NC=1/C=C1/C(C)=C(C=C)C(N/1)=O.[CH3:44][CH2:45][C:46]1[C:68]([CH3:69])=[C:67]2[NH:70][C:47]=1[CH:48]=[C:49]1[N:102]=[C:101]3[C:51]([C:52]([C@H:54]([C:103]([O:105][CH3:106])=[O:104])[C:55]3=[C:56]3[N:60]=[C:59]([CH:61]=[C:62]4[NH:71][C:65](=[CH:66]2)[C:64]([CH:72]=[CH2:73])=[C:63]4[CH3:74])[C@@H:58]([CH3:75])[C@@H:57]3[CH2:76][CH2:77][C:78]([O:80][CH2:81]/C=C(/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\C)=[O:79])=[O:53])=[C:50]1[CH3:107].S(=O)(=O)(O)O.ClCCl>CO>[CH3:44][CH2:45][C:46]1[C:47]2=[N:70][C:67](=[CH:66][C:65]3[NH:71][C:62]([CH:61]=[C:59]4[CH:58]([CH3:75])[CH:57]([CH2:76][CH2:77][C:78]([O:80][CH3:81])=[O:79])[C:56]([C:55]5[CH:54]([C:103]([O:105][CH3:106])=[O:104])[C:52](=[O:53])[C:51]6[C:101]=5[NH:102][C:49]([C:50]=6[CH3:107])=[CH:48]2)=[N:60]4)=[C:63]([CH3:74])[C:64]=3[CH:72]=[CH2:73])[C:68]=1[CH3:69]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 5280352BilirubinHCID 178435491HCID 178435491, compound

Product 1

HCID 178435494HCID 178435494, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The green filtrate was evaporated and purified by flash chromatography on Grade V neutral Alumina, eluting first with n-hexane to remove a fast running yellow band and then with dichloromethane to obtain the major blue/gray peak containing pheophytin-a. Treatment of pheophytin-a with 500 ml sulfuric acid in methanol for 12 hours at room temperature in the dark under nitrogen was followed by dilution with dichloromethane. The reaction mixture was rinsed with water and then 10% aqueous sodium bicarbonate and the organic layer was dried, evaporated, and the residue recrystallized from dichloromethane/methanol to obtain 1.8 gm methyl pheophorbide-a. Methyl pheophorbide-a appears to be inactive in the in vivo tumoricidal activity assay when injected at a dose of 5 mg/kg.

Workup

  1. customThe green filtrate was evaporated
  2. custompurified by flash chromatography on Grade V neutral Alumina
  3. washeluting first with n-hexane
  4. customto remove
  5. customwith dichloromethane to obtain the major blue/gray peak
  6. washThe reaction mixture was rinsed with water
  7. dry with material10% aqueous sodium bicarbonate and the organic layer was dried
  8. customevaporated
  9. customthe residue recrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-c41eece4b4f94e4ebfe66e833887660b
Source dataset
uspto-grants-2006_02
Patent number
USRE038994E1

Reaction notes

Loading…