Phenethylamine → HCID 86739540, compound

HRID 1462481Notes

Reaction equation

HRID 1462481 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 2 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-2880832c3de743708163ff737e782bd3
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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