Trifluoroacetic acid → HCID 9798637, compound

HRID 1976454Notes

Reaction equation

HRID 1976454 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]#[C:26][CH3:27])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]([C:28](=[O:31])[NH:29][OH:30])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:30][NH:29][C:28]([CH:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]#[C:26][CH3:27])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9890137HCID 9890137, compound

Product 1

HCID 9798637HCID 9798637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.147 g (0.325 mmol) of the product of Example 58, 4-(4-but-2-ynyloxy-benzenesulfonyl)-3-hydroxycarbamoyl-piperazine-1-carboxylic acid tert-butyl ester, in 3.0 mL of dichloromethane was added 0.3 mL of trifluoroacetic acid and the reaction was stirred at room temperature for 1 h. The reaction was then concentrated in vacuo and the residue was diluted with dichloromethane. The organics were washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.053 g of 1-(4-but-2-ynyloxy-benzenesulfonyl)-piperazine-2-carboxylic acid hydroxyamide as a tan solid. Electrospray Mass Spec 354.2 (M+H)+

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. additionthe residue was diluted with dichloromethane
  3. washThe organics were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c58e915601c34c3b8beb23b708843ba8
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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