Trifluoroacetic acid → HCID 67396190, compound
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[N:26]=[C:25]([CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=3)[O:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:38][O:37][C:31]1[CH:30]=[C:29]([CH:28]=[CH:27][C:25]2[O:24][N:23]=[C:22]([CH2:21][CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)[N:26]=2)[CH:34]=[CH:33][C:32]=1[O:35][CH3:36]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Trifluoroacetic acid (5 mL) was added slowly into a solution of 4-{5-[2-(3,4-dimethoxy-phenyl)-vinyl]-[1,2,4]oxadiazol-3-ylmethyl}-piperidine-1-carboxylic acid tert-butyl ester (compound of Example 18; 4.5 g, 10.4 mmol) in dichloromethane (25 mL) and was stirred at 25° C. for 15 h. The solvent was evaporated and the residue was extracted into chloroform (2×25 mL). The combined organic layers were washed with saturated sodium carbonate solution (2×25 mL) and water (1×25 mL). The organic phase obtained was dried over anhydrous sodium sulphate and concentrated to afford the title compound.
Workup
- customThe solvent was evaporated
- extractionthe residue was extracted into chloroform (2×25 mL)
- washThe combined organic layers were washed with saturated sodium carbonate solution (2×25 mL) and water (1×25 mL)
- customThe organic phase obtained
- dry with materialwas dried over anhydrous sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-59b3371814754f8a95316be33a44fe4a
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629277B2
Reaction notes
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