7-demethylmitomycin A → Mitomycin A

HRID 1651309Notes

Reaction equation

HRID 1651309 reaction equation
[CH3:1][C:2]1[C:22](=[O:23])[C:20](=[O:21])[C:5]2[C@@H:6]([CH2:15][O:16][C:17]([NH2:19])=[O:18])[C@@:7]3([O:13][CH3:14])[C@H:11]4[NH:12][C@H:10]4[CH2:9][N:8]3[C:4]=2[C:3]=1[OH:24].[CH3:25]NN=NC1C=CC(C)=CC=1.C(Cl)Cl.CO>C(Cl)Cl.C(OCC)C>[CH3:1][C:2]1[C:3](=[O:24])[C:4]2[N:8]3[C@@:7]([O:13][CH3:14])([C@H:6]([CH2:15][O:16][C:17]([NH2:19])=[O:18])[C:5]=2[C:20](=[O:21])[C:22]=1[O:23][CH3:25])[C@H:11]1[NH:12][C@H:10]1[CH2:9]3

Participants

6

Reactant 3

HCID 117273937-demethylmitomycin AHCID 21226129Dichloromethane methanolHCID 178486252HCID 178486252, compound

Product 1

HCID 19972Mitomycin AYield 24%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A 100 mg (0.30 mmole) quantity of 7-hydroxy9a-methoxymitosane and 100 mg (0.67 mmole) quantity of 3-methyl-1-p-tolyltriazene was dissolved in 2 ml methylene chloride and 10 ml diethyl ether. The solution, after gently refluxing for 6 hours was stirred at room temperature for 18 hours. TLC [methylene chloride:methanol (90:10)] revealed the appearance of a deep purple spot at Rf =0.36 with a trace amount of impurity at Rf =0.41. The reaction mixture was concentrated to dryness and chromatographed on Woelm neutral alumina employing methylene chloride and methylene chloride:methanol (30:1) as eluting solvents. Fractions containing the component at Rf =0.36 were pooled and concentrated to dryness. Precipitation of the dry residue from methylene chloride and hexane afforded the title compound as a fine amorphous purple powder (25 mg, 24%), mp 161°.

Workup

  1. temperatureThe solution, after gently refluxing for 6 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customchromatographed on Woelm neutral alumina
  4. washas eluting solvents
  5. additionFractions containing the component at Rf =0.36
  6. concentrationconcentrated to dryness
  7. customPrecipitation of the dry residue from methylene chloride and hexane

Sources & evidence

ORD record
ord-480c8c1748244af4b03d1d62ac2e5443
Source dataset
uspto-grants-1990_05
Patent number
US04927943

Reaction notes

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