2-(Trifluoromethyl)benzoic acid → 3-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid ethyl ester
Reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=O.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:46]([O:48][C:49](=[O:59])[CH2:50][C:51](=[O:58])[N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)[CH3:47]>CN(C=O)C.O>[CH2:46]([O:48][C:49](=[O:59])[CH2:50][C:51](=[O:58])[N:52]1[CH2:57][CH2:56][N:55]([C:24](=[O:26])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[C:21]([F:20])([F:32])[F:31])[CH2:54][CH2:53]1)[CH3:47]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
HOBt (1.38 g, 10.2 mmol) and DIPEA (3.68 mL, 21.3 mmol) were added to a stirred solution of 2-trifluoromethyl-benzoic acid (1.62 g, 8.5 mmol) in DMF (5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (1.96 g, 10.2 mmol) followed by 3-oxo-3-piperazin-1-yl-propionic acid ethyl ester hydrochloride (2 g, 8.5 mmol) were added. The reaction mixture was stirred at the room temperature overnight, then diluted with water and the product extracted with Ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography using silica gel 60-120 mesh (50% ethyl acetate in hexane) to afford 1.5 g (48%) of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid ethyl ester. LCMS: 373.13 (M+1)+, 90%
Workup
- additionwere added
- extractionthe product extracted with Ethyl acetate
- washThe ethyl acetate was washed with brine solution
- dry with materialdried over Na2SO4
- customevaporated to dryness
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-275bfa7ab96547a898d764faf7d5b16a
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039463B2
Reaction notes
Loading…