Mitomycin A → HCID 86739538, compound

HRID 1462480Notes

Reaction equation

HRID 1462480 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.[NH2:26][CH2:27][C:28]([NH2:30])=[O:29]>C(O)C>[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:26][CH2:27][C:28]([NH2:30])=[O:29])=[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

4

Reactant 2

HCID 19972Mitomycin AHCID 69020Glycinamide

Product 1

HCID 86739538HCID 86739538, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of mitomycin A (40 mg, 0.11 mmol) and glycinamide (42 mg) in 3.5 ml of absolute ethanol was stirred at room temperature for 4 hours. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography using a pre-coated silica-gel plate (2 mm thickness) and a mixture of ethanol and ethyl acetate (1:3 by volume) as developing solvent. The blue zone was eluted with ethanol and evaporated under reduced pressure to give 12.8 mg (29.7% yield) of the desired product having a melting point of 124°-126° C. and providing the following analysis:

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by preparative thin-layer chromatography
  3. additiona mixture of ethanol and ethyl acetate (1:3 by volume)
  4. washThe blue zone was eluted with ethanol
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ffd9fbd1fba8492ca45fe50e3a980776
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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