Ethylacetate heptane → HCID 49847348, compound

HRID 874573Notes

Reaction equation

HRID 874573 reaction equation
[OH:1][NH:2][C:3]([C@@H:5]([N:30]1[CH2:35][CH2:34][N:33](C(OCC2C=CC=CC=2)=O)[CH2:32][CH2:31]1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[O:4].CCCCCCC.C(OCC)(=O)C>ClCCl.FC(F)(F)C(O)=O>[OH:1][NH:2][C:3](=[O:4])[C@@H:5]([N:30]1[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 21899848Ethylacetate heptaneHCID 49849201HCID 49849201, compound

Product 1

HCID 49847348HCID 49847348, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

90 mg (0.15 mmol) of benzyl 4-((S)-1-hydroxycarbamoyl-2-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]ethyl)piperazine-1-carboxylate are placed in solution in 5 ml of dichloromethane and 5 ml of trifluoroacetic acid. The reaction medium is then stirred at ambient temperature for 96 h. After evaporation of the trifluoroacetic acid, the residue is taken up with 5 ml of saturated aqueous solution of sodium hydrogen carbonate and extracted with n-butanol. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product obtained is taken up in a 50/50 heptane/ethyl acetate mixture, stirred for 1 h and then filtered and dried under vacuum. 50 mg (70%) of (S)-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-piperazin-1-ylpropionamide are obtained in the form of a beige solid with a melting point of 225° C.

Workup

  1. customAfter evaporation of the trifluoroacetic acid
  2. extractionextracted with n-butanol
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. stirringstirred for 1 h
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-4651d8f7ed0e4919b3fae0064f4c50f2
Source dataset
uspto-grants-2015_03
Patent number
US08980897B2

Reaction notes

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