Lithium hydroxide, monohydrate → 3-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

HRID 1665613Notes

Reaction equation

HRID 1665613 reaction equation
O[Li].O.C([O:6][C:7](=[O:29])[CH2:8][C:9](=[O:28])[N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:12][CH2:11]1)C>CO.C1COCC1.O>[O:28]=[C:9]([N:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:14][CH2:15]1)[CH2:8][C:7]([OH:29])=[O:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 578758243-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid ethyl ester

Product 1

HCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acidYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (400 mg, 9.5 mmol) was added to a solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid ethyl ester (1.4 g, 3.8 mmol) in methanol (10 mL), THF (4 mL) and H2O (10 mL) and the resulting mixture was stirred for 2 hours at room temperature. The mixture was and the residue was diluted with water, washed with diethyl ether, acidified with concentrated HCl, extracted with ethyl acetate and evaporated to dryness. The residue was recrystallized from hexane to afford 1.2 g (92%) of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid. LCMS: 345.1 (M+1)+, 96%

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. customevaporated to dryness
  4. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-1c74b5daac1c4d43b1fd1a79744c0757
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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