Methanol → HCID 86737736, compound

HRID 476652

Reaction equation

HRID 476652 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][OH:27]>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:27][CH:26]=[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

4

Reactant 2

HCID 887MethanolHCID 19972Mitomycin A

Product 1

HCID 86737736HCID 86737736, compoundYield 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 hexane gave 30 mg (42.7% yield) of the desired product as purple-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
  7. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-6695317cff2e4ca1939b1de3423387a9
Source dataset
uspto-grants-1989_12
Patent number
US04885304

Linked notes

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