3-Amino-1-propanol → HCID 86737744, compound

HRID 476664Notes

Reaction equation

HRID 476664 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.[OH:26][CH2:27][CH2:28][CH2:29][NH2:30]>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:30][CH2:29][CH2:28][CH2:27][OH:26])=[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 90863-Amino-1-propanolHCID 19972Mitomycin A

Product 1

HCID 86737744HCID 86737744, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 60 mg mitomycin A (0.17 mmol) in 5 ml of anhydrous methanol was added with stirring 0.5 ml of 3-hydroxypropylamine. The progress of the reaction was checked by TLC and the reaction appeared to be complete in two hours. The solvent was removed by evaporation under reduced pressure. The residue was dissolved in 100 ml of ethyl acetate and the organic layer waswashed with water, dried over anhydrous sodium sulfate, and the solvent was removed by evaporating under reduced pressure. The residue was then chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column with a mixture of ethyl acetate and acetone (9:1 by volume) was evaporated to dryness under reduced pressure. Recrystallization from acetone gave 60.7 mg (91% yield) of the desired product as purple crystals having a melting point of >250° (decomposing and providing the following analysis:

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customby evaporating under reduced pressure
  6. customThe residue was then chromatographed
  7. customThe fraction obtained
  8. washby eluting the column
  9. additionwith a mixture of ethyl acetate and acetone (9:1 by volume)
  10. customwas evaporated to dryness under reduced pressure
  11. customRecrystallization from acetone

Sources & evidence

ORD record
ord-1360163e87c5425ba0ff66d8875cc75b
Source dataset
uspto-grants-1989_12
Patent number
US04885304

Reaction notes

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