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

HRID 1462472Notes

Reaction equation

HRID 1462472 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.[CH3:26][NH:27][CH2:28][C:29]#[CH:30]>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]([N:27]([CH2:28][C:29]#[CH:30])[CH3:26])=[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]

Participants

4

Reactant 2

HCID 19972Mitomycin AHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 867377421,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(N-methylpropargylamino)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamateYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg (0.14 mmol) of mitomycin A in 10 ml of anhydrous methanol was stirred with 150 mg (2 mmol) of N-methylpropargylamine at room temperature. The reaction appeared to be completed in 3 hours, as revealed by TLC. The solvent was removed by evaporation under reduced pressure and the residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column with ethyl acetate was evaporated under reduced pressure. Recrystallization from a mixture of methylene chloride and hexane gave 20 mg (37% yield) of the desired product as purple-colored crystals having a melting point of 86°-87° C. (decomposing) and providing the following analysis:

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue was chromatographed
  3. customThe fraction obtained
  4. washby eluting the column with ethyl acetate
  5. customwas evaporated under reduced pressure
  6. customRecrystallization
  7. additionfrom a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-da276a6d3e2040068ff908658aea6221
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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