Carbon Dioxide → 8a-Hydroxy-6-methoxy-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 444389Notes

Reaction equation

HRID 444389 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[O:24][CH3:25])[C@H:13]1[N:22]([CH3:23])[C@H:12]1[CH2:11]3.CC(C)([O-])C.[K+].C(=O)=O>O1CCOCC1>[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[O:24][CH3:25])[C@H:13]1[N:22]([CH3:23])[C@H:12]1[CH2:11]3

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 19973Mitomycin BHCID 23665647Potassium tert-butoxide

Product 1

HCID 1732508a-Hydroxy-6-methoxy-1,5-dimethyl-8-methylidene-1,1a,2,8,8a,8b-hexahydroazireno[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dioneYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In this example, 100 mg of mitomycin B is dissolved in 5 ml of dioxane. To this solution, 100 mg of potassium t-butoxide is added and the mixture is stirred at room temperature for 2 days. The reaction mixture is then neutralized with an excess amount of dry ice and subjected to filtration. The filtrate is concentrated under reduced pressure and the residue is then subjected to silica gel column chromatography using a mixed solvent of acetone and chloroform (1:4) (volume ratio as is the same hereinafter) as a developer. Fractions of eluate which have a high Rf value and are blue are combined and concentrated under reduced pressure. The residue is crystallized from acetone and petroleum ether to obtain 14 mg of the desired compound (yield 17.0%) as purplish black needle-like crystals having the following physical properties.

Workup

  1. filtrationsubjected to filtration
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is crystallized from acetone and petroleum ether

Sources & evidence

ORD record
ord-8260773de63342a8b37ebc9d8e42b945
Source dataset
uspto-grants-1981_04
Patent number
US04264504

Reaction notes

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