4-Aminophenol → [6-(4-Hydroxyanilino)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl hydrogen carbonimidate

HRID 224230

Reaction equation

HRID 224230 reaction equation
[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.[CH:26]1[C:31]([NH2:32])=[CH:30][CH:29]=[C:28]([OH:33])[CH:27]=1>CO>[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]=1[NH:32][C:31]1[CH:26]=[CH:27][C:28]([OH:33])=[CH:29][CH:30]=1)[CH:13]1[NH:23][CH:12]1[CH2:11]3

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 19972Mitomycin A

Product 1

HCID 51036[6-(4-Hydroxyanilino)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl hydrogen carbonimidateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mitomycin A (1 g) and p-aminophenol (2 g) are added to methanol (100 ml) and the mixture is stirred for 5 hours at room temperature. After completion of the reaction, the reaction solution is concentrated under reduced pressure and then dried in vacuo. The dried product is then subjected to silica gel column chromatography developed by acetone-chloroform mixture (1:1) and recrystallized from an acetone-ether mixture to obtain a desired product (950 mg) in the form of green needle crystals with a yield of 78%. This product shows a green spot (Rf=0.1) by silica gel thin layer chromatography using acetone-chloroform mixture (1:1) as developer. The product does not show a precise melting point.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution is concentrated under reduced pressure
  3. customdried in vacuo
  4. customrecrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-173f724d470143d3bb544f3c64259595
Source dataset
uspto-grants-1980_11
Patent number
US04231936

Linked notes

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