Trifluoroacetic acid → Dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-piperazin-1-ylmalonate

HRID 874549Notes

Reaction equation

HRID 874549 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]([CH2:30][NH:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]#[C:44][CH3:45])=[CH:37][CH:36]=2)(=[O:34])=[O:33])([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:24][CH3:25])=[O:23])[CH2:17][CH2:16]1)=O)(C)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH2:42]([O:41][C:38]1[CH:39]=[CH:40][C:35]([S:32]([NH:31][CH2:30][C:21]([N:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)([C:22]([O:24][CH3:25])=[O:23])[C:26]([O:28][CH3:29])=[O:27])(=[O:34])=[O:33])=[CH:36][CH:37]=1)[C:43]#[C:44][CH3:45]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71115388Dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]malonate

Product 1

HCID 71115173Dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-piperazin-1-ylmalonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 ml of trifluoroacetic acid are added to a solution of 2.1 g (4 mmol) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]malonate diluted in 30 ml of dichloromethane. After stirring at ambient temperature for 24 h, a saturated aqueous solution of sodium hydrogen carbonate is added to pH=8 and the reaction medium is extracted with dichloromethane. The organic phases are combined, washed with water, dried over magnesium sulfate, and then filtered and evaporated. 1.7 g (98%) of dimethyl 2-[(4-but-2-ynyloxybenzenesulfonylamino)methyl]-2-piperazin-1-ylmalonate are obtained in the form of a white solid.

Workup

  1. extractionthe reaction medium is extracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0d43f360bcdb42e1817e13cf4bc5dc1b
Source dataset
uspto-grants-2015_03
Patent number
US08980897B2

Reaction notes

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