(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 88629345, compound

HRID 2287069Notes

Reaction equation

HRID 2287069 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.Cl.[Cl:28][CH2:29][CH2:30][NH2:31].C([O-])(=O)C.[Na+]>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:31][CH2:30][CH2:29][Cl:28])=[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

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 97937372-Chloroethylamine hydrochloride

Product 1

HCID 88629345HCID 88629345, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 33 mg (0.09 mmol) of N-methylmitomycin A in 5 ml of anhydrous methanol, a solution of 56 mg of 2-chloroethylamine hydrochloride (0.5 mmol) in 2.5 ml of methanol and a solution of 41 mg sodium acetate (0.5 mmol) in 2.5 ml of methanol were added alternatively with constant stirring over a period of 10 minutes. The stirred reaction mixture was checked frequently by TLC and the reaction appeared to be complete in 24 hours. The solvent was evaporated and the residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column with ethyl acetate was evaporated under reduced pressure. Recrystallization from a mixture of chloroform and hexane gave 16 mg (38% yield) of the desired product as purple-colored crystals having a melting point of 73°-74° C. (decomposing) and providing the following analysis:

Workup

  1. customThe stirred reaction mixture
  2. waitto be complete in 24 hours
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed
  5. customThe fraction obtained
  6. washby eluting the column with ethyl acetate
  7. customwas evaporated under reduced pressure
  8. customRecrystallization
  9. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-632a33afeadb458a8842ce98f16a394a
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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