Potassium Carbonate → HCID 20231541, compound

HRID 2290644Notes

Reaction equation

HRID 2290644 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:26]([CH:28]1[CH2:30][NH:29]1)#[N:27].C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:18](=[O:17])([OH:19])[NH2:20].[OH:17][CH2:16][CH:15]1[C:6]2[C:4](=[O:5])[C:3]([N:29]3[CH2:30][CH:28]3[C:26]#[N:27])=[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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19972Mitomycin AHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 20231541HCID 20231541, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of mitomycin A (100 mg. or 0.286 mmol) in 8 ml of anhydrous methanol was treated with 2-cyanoaziridine (38.9 mg. or 0.572 mmol) and 30 mg. of potassium carbonate, under nitrogen at room temperature. When thin-layer chromatography on silica gel (2:8 methanol-chloroform as solvent) showed that starting material was no longer present, the mixture was diluted with 50 ml of methylene chloride, filtered, and evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography on silica gel with a mixture of methanol and chloroform (2:8 by volume) as the solvent. This procedure gave 33 mg. (30% yield) of the desired product having a melting point of 87°-89° C. (decomposing) and providing the following analysis:

Workup

  1. customat room temperature
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe residue was purified by preparative thin-layer chromatography on silica gel with a mixture of methanol and chloroform (2:8 by volume) as the solvent
  5. customThis procedure gave 33 mg

Sources & evidence

ORD record
ord-62cb358aa2e045cfb93bcf1f83bcb398
Source dataset
uspto-grants-1986_10
Patent number
US04617389

Reaction notes

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