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

HRID 1462466Notes

Reaction equation

HRID 1462466 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.C(Cl)(Cl)Cl.[CH3:30][OH:31]>C(N)C1OC=CC=1>[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:10][CH2:7][C:6]3[O:31][CH:30]=[CH:3][CH:4]=3)=[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

5

Reactant 3

HCID 887MethanolHCID 6212ChloroformHCID 19972Mitomycin A

Product 1

HCID 867377361,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-furfurylamino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamateYield 42.7%

Reagents, catalysts & solvents 1

HCID 3438FurfurylamineSolvent

Procedure

To a solution of 60 mg (0.17 mmol) of mitomycin A in 8 ml of anhydrous methanol, 0.5 ml of furfurylamine was added with stirring. The progress of the reaction was periodically checked by TLC and the reaction appeared to be complete in 3 hours. 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. Recrystallization from a mixture of chloroform and here gave 30 mg (42.7% yield) of the desired product as colored crystals having a melting point of 62°-63° (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
  6. customRecrystallization

Sources & evidence

ORD record
ord-88df190deead4a0187b61068ab590d5d
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

Loading…