Methanol → HCID 19838041, compound

HRID 2287061Notes

Reaction equation

HRID 2287061 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[N:23]([CH3:24])[C@H:12]1[CH2:11]3.[CH3:27][OH:28]>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:28][CH:27]=[CH:3][CH:4]=3)=[C:2]([CH3:1])[C:8](=[O:9])[C:7]=2[N:10]2[CH2:11][CH:12]3[N:23]([CH3:24])[CH:13]3[C:14]12[O:21][CH3:22]

Participants

4

Reactant 2

HCID 887MethanolHCID 159845(6,8a-Dimethoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl hydrogen carbonimidate

Product 1

HCID 19838041HCID 19838041, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 3438FurfurylamineSolvent

Procedure

To a solution of 50 mg (0.13 mmol) of N-methylmitomycin A in 6 ml of anhydrous methanol, 0.5 ml of furfurylamine was added with stirring. 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 a mixture of chloroform and ethyl acetate (1:1 by volume) was evaporated under reduced pressure. Recrystallization from a mixture of chloroform and hexane gave 31 mg (55.7% yield) of the desired product as purple colored crystals having a melting point of 140°-141° (decomposing) and providing the following analyses:

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
  5. additionwith a mixture of chloroform and ethyl acetate (1:1 by volume)
  6. customwas evaporated under reduced pressure
  7. customRecrystallization
  8. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-646baaeb97784c31bd29e3645aa62c18
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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