1,5-Diazabicyclo(5,4,0)undec-5-ene → 6-Amino-8a-hydroxy-1,5-dimethyl-8-methylidene-1,1a,2,8,8a,8b-hexahydroazireno[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione

HRID 1075306Notes

Reaction equation

HRID 1075306 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([OH:21])([C@H:15]([CH2:16]OC(N)=O)[C:6]=2[C:4](=[O:5])[C:3]=1[NH2:24])[C@H:13]1[N:22]([CH3:23])[C@H:12]1[CH2:11]3.N12CCCCC1C=NCCC2>O1CCCC1>[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([OH:21])([C:15](=[CH2:16])[C:6]=2[C:4](=[O:5])[C:3]=1[NH2:24])[C@H:13]1[N:22]([CH3:23])[C@H:12]1[CH2:11]3

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 303406179026-43-0

Product 1

HCID 1732516-Amino-8a-hydroxy-1,5-dimethyl-8-methylidene-1,1a,2,8,8a,8b-hexahydroazireno[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dioneYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-epi-mitomycin D (10 mg) was dissolved in tetrahydrofuran (0.5 ml). To the solution was added 1,5-diazabicyclo[5,4,0]undec-5-ene (20 mg) and the solution was refluxed for 18 hours. After completion of the reaction, the solvent was removed by evaporation in vacuo, and the residue was purified by silica gel column chromatography using a solvent system of chloroform and acetone (3:2 v/v) to give the desired dark green needle crystals (4.4 mg; yield 53.8%) having the following physical characteristics.

Workup

  1. temperaturethe solution was refluxed for 18 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by evaporation in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. customto give the desired dark green needle crystals (4.4 mg; yield 53.8%)

Sources & evidence

ORD record
ord-f51c8a63daa24aa38120393bbede81e3
Source dataset
uspto-grants-1983_07
Patent number
US04395558

Reaction notes

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