Sulfuric Acid → HCID 178435494, Verbindung

HRID 891828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891828
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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 178435494HCID 178435494, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c41eece4b4f94e4ebfe66e833887660b
Quelldatensatz
uspto-grants-2006_02
Patentnummer
USRE038994E1

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