Hydrogen chloride-ethyl acetate → N-[(1S)-1-methyl-2-({1-[6-(2-methylpropoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)ethyl]acetamide
Reaction equation
[CH3:1][C@H:2]([NH:25][C:26](=O)[O:27]C(C)(C)C)[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:7][CH2:6]1.Cl.[C:34](OCC)(=O)C>>[CH3:1][C@H:2]([NH:25][C:26](=[O:27])[CH3:34])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([O:20][CH2:21][CH:22]([CH3:23])[CH3:24])[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:7][CH2:6]1Participants
3
Procedure
To tert-butyl [(1S)-1-methyl-2-({1-[6-(2-methylpropoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)ethyl]carbamate (97 mg) was added 4 M hydrogen chloride/ethyl acetate (5 mL), and the mixture was stirred at room temperature for 15 min and concentrated. To the residue were added pyridine (5 mL) and acetic anhydride (5 mL), and the mixture was stirred at room temperature for 15 min. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/methanol), and recrystallized from ethyl acetate/hexane to give the title compound (52 mg).
Workup
- concentrationconcentrated
- additionTo the residue were added pyridine (5 mL) and acetic anhydride (5 mL)
- stirringthe mixture was stirred at room temperature for 15 min
- concentrationThe reaction solution was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (ethyl acetate/methanol)
- customrecrystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-dc5c39e8fb214a42bec87f3a776de222
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703758B2
Reaction notes
Loading…