(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 → HCID 88629851, compound

HRID 476663Notes

Reaction equation

HRID 476663 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14](OC)([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.[C:27]([O-])(=O)C.[Na+].Cl.[OH:33][CH2:34][CH2:35][CH2:36][NH2:37]>CO>[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:37][CH2:36][CH2:35][CH2:34][OH:33])=[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[CH3:27]

Participants

5

Reactant 3

HCID 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 carbonimidateHCID 517045Sodium AcetateHCID 30148263-Aminopropan-1-ol hydrochloride

Product 1

HCID 88629851HCID 88629851, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 50 mg (0.13 mmol) of N-methylmitomycin A in 10 ml of anhydrous methanol, a solution of 82 mg (1 mmol) sodium acetate in 2.5 ml of methanol and a solution of 130 mg (1 mmol) of 3-hydroxypropylamine hydrochloride in 2.5 ml of methanol were added alternatively with vigorous stirring, over a period of 10 minutes. The progress of the stirred reaction was checked frequently by TLC and appeared to be complete in 24 hours. The solvent was evaporated 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 methylene chloride and hexane gave 31 mg. (61% yield) of the desired product as purple-colored crystals having a melting point of 139°-140° (decomposing) and providing the following analysis:

Workup

  1. customThe progress of the stirred reaction
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was chromatographed
  4. customThe fraction obtained
  5. washby eluting the column with ethyl acetate
  6. customwas evaporated
  7. customRecrystallization
  8. additionfrom a mixture of methylene chloride and hexane
  9. customgave 31 mg

Sources & evidence

ORD record
ord-a97766e0d2cf4d0aa9bce7fe6a4dd051
Source dataset
uspto-grants-1989_12
Patent number
US04885304

Reaction notes

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