Phenethylamine → HCID 86739540, compound

HRID 476668Notes

Reaction equation

HRID 476668 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]1([CH2:32][CH2:33][NH2:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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:34][CH2:33][CH2:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[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 1001PhenethylamineHCID 19972Mitomycin A

Product 1

HCID 86739540HCID 86739540, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 115 mg of mitomycin A (0.33 mmol) in 4 ml of anydrous methanol was added with stirring 80 mg of phenylethylamine (0.66 mmol) in 1 ml of anhydrous methanol. After 18 hours, the solvent was removed by evaporation under reduced pressure. The residue was dissolved in 15 ml of ethyl acetate, and then washed with five 15 ml portions of pH 4 buffer solution. The solvent was removed under reduced pressure and the residue was chromatographed using silica gel as adsorbent and ethyl acetate as solvent. Recrystallization of the product from ethyl acetate-ether gave 85 mg (58.7% yield) of purple solid having a melting point of 94°-96° C. and providing the following analysis:

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in 15 ml of ethyl acetate
  3. washwashed with five 15 ml portions of pH 4 buffer solution
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed
  6. customRecrystallization of the product from ethyl acetate-ether

Sources & evidence

ORD record
ord-31408954e7fe4748ba40886d4b193662
Source dataset
uspto-grants-1989_12
Patent number
US04885304

Reaction notes

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