Mitomycin A → 1,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-methylallylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate

HRID 476657

Reaktionsgleichung

Reaktionsgleichung von HRID 476657
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1OC)[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.[CH3:26][C:27](=[CH2:30])[CH2:28][NH2:29]>CO>[C:18](=[O:17])([OH:19])[NH2:20].[OH:17][CH2:16][CH:15]1[C:6]2[C:4](=[O:5])[C:3]([NH:29][CH2:28][C:27]([CH3:30])=[CH2:26])=[C:2]([CH3:1])[C:8](=[O:9])[C:7]=2[N:10]2[CH2:11][CH:12]3[NH:23][CH:13]3[C:14]12[O:21][CH3:22]

Komponenten

4

Edukt 2

HCID 19972Mitomycin AHCID 761412-Methylallylamine

Produkt 1

HCID 198380521,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-methylallylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamateAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 50 mg mitomycin A (0.138 mmol) in 8 ml. of anhydrous methanol was stirred with 29 mg of 2-methylallylamine. The progress of the reaction was periodically checked by TLC and, after 2 hours, the solvent was removed by evaporation under reduced pressure and the residue was purified by column chromatography using silica-gel as adsorbent and ethyl acetate as the eluant. Recrystallization from a mixture of chloroform and hexane gave 30 mg (55% yield) of the desired product as purple crystals having a melting point of >250° C. (decomposing) and providing the following analysis:

Aufarbeitung

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography
  3. customRecrystallization
  4. additionfrom a mixture of chloroform and hexane

Quellen und Nachweise

ORD-Eintrag
ord-164a7a821f6048f9b0d26bd2ae410984
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04885304

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