Hydrogen chloride-ethyl acetate → N-[(1S)-2-({1-[6-(cyclobutylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]acetamide
Reaction equation
[CH:1]1([CH2:5][O:6][C:7]2[CH:33]=[CH:32][C:10]3[N:11]=[C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])OC(C)(C)C)[CH3:23])[CH2:16][CH2:15]4)[O:13][C:9]=3[CH:8]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[C:35](OCC)(=O)C>>[CH:1]1([CH2:5][O:6][C:7]2[CH:33]=[CH:32][C:10]3[N:11]=[C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])[CH3:35])[CH3:23])[CH2:16][CH2:15]4)[O:13][C:9]=3[CH:8]=2)[CH2:4][CH2:3][CH2:2]1Participants
3
Procedure
To tert-butyl [(1S)-2-({1-[6-(cyclobutylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate (130 mg) was added 4M hydrogen chloride/ethyl acetate (5 mL), and the mixture was stirred at room temperature for 15 min and concentrated. Pyridine (5 mL) and acetic anhydride (5 mL) were added to the residue, and the mixture was stirred at room temperature for 15 min. The reaction mixture 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 (73 mg).
Workup
- concentrationconcentrated
- additionPyridine (5 mL) and acetic anhydride (5 mL) were added to the residue
- stirringthe mixture was stirred at room temperature for 15 min
- concentrationThe reaction mixture 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-568b3ca4cf0849f1b83c16359993d510
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703758B2
Reaction notes
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