Allylamine → HCID 86737740, compound

HRID 476656

Reaction equation

HRID 476656 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.[CH2:26]([NH2:29])[CH:27]=[CH2:28]>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:29][CH2:26][CH:27]=[CH2:28])=[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 7853AllylamineHCID 19972Mitomycin A

Product 1

HCID 86737740HCID 86737740, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.28 mmol) of mitomycin A in 8 ml of anhydrous methanol, 150 mg (2.6 mmol) of allylamine was added with constant stirring. The reaction mixture was stirred overnight whereupon TLC indicated the absence of starting material. The solvent was then evaporated under reduced pressure and the residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column from ethyl acetate was evaporated under reduced pressure. Recrystallization from a mixture of methylene chloride and hexane gave 29 mg (27.0% yield) of the desired product as purple-colored crystals having a melting point of 81°-82° (decomposing) and providing the following analysis:

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customthe residue was chromatographed
  3. customThe fraction obtained
  4. washby eluting the column from ethyl acetate
  5. customwas evaporated under reduced pressure
  6. customRecrystallization
  7. additionfrom a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-16a35ad9e8e9478d83cb6cfa76ba86dc
Source dataset
uspto-grants-1989_12
Patent number
US04885304

Linked notes

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