Trifluoroacetic acid → Ethyl 4-(2-(methylamino)ethyl)benzoate
Reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:6][NH:8][CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 0.907 g (2.95 mmol) of ethyl 4-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)benzoate in 10 mL of DCM at 0° C. was added 2.0 mL (26 mmol) of trifluoroacetic acid (TFA). The reaction was warmed to 22° C., stirred for 3 h and the solvents were then evaporated. The residue was partitioned between 100 mL of ethyl acetate and 100 mL of 1 N NaOH which had been saturated with NaCl. The aqueous layer was back-extracted with ethyl acetate (6×50 mL) and the combined organics were dried (Na2SO4) and evaporated to give 2c as a colorless oil.
Workup
- customthe solvents were then evaporated
- customThe residue was partitioned between 100 mL of ethyl acetate and 100 mL of 1 N NaOH which
- extractionThe aqueous layer was back-extracted with ethyl acetate (6×50 mL)
- dry with materialthe combined organics were dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-c5ff739a42c64004be5f2bf31cda68b2
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227918B2
Reaction notes
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