Mitomycin A → HCID 19838045, compound

HRID 2287070Notes

Reaction equation

HRID 2287070 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([O-])(=O)C.[Na+].Cl.[Cl:32][CH2:33][CH2:34][NH2:35]>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:35][CH2:34][CH2:33][Cl:32])=[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

5

Reactant 3

HCID 19972Mitomycin AHCID 517045Sodium AcetateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 19838045HCID 19838045, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 100 mg mitomycin A (0.286 mmol) in 10 ml. of anhydrous methanol, a solution of 82 mg sodium acetate (1 mmol) in 2.5 ml. of methanol and a solution of 116 mg 2-chloroethylamine hydrochloride (1 mmol) in 2.5 ml. of methanol were added alternatively with constant stirring, over a period of ten minutes. The stirred reaction mixture was periodically checked by TLC and the reaction appeared to be complete in 24 hours. The insoluble sodium chloride was removed by filtration and the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography using ethyl acetate and acetone (4:1 by volume) as the eluant. Recrystallization from a mixture of chloroform and hexane gave 34 mg. (30% yield) of the desired product as purple-colored crystals having a melting point of 59° C. (decomposing) and providing the following analysis:

Workup

  1. customThe stirred reaction mixture
  2. customThe insoluble sodium chloride was removed by filtration
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography
  5. customRecrystallization
  6. additionfrom a mixture of chloroform and hexane
  7. customgave 34 mg

Sources & evidence

ORD record
ord-907fd6269b2c4f599b4bae3b3a05ba5c
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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