Hydrogen chloride-ethyl acetate → N-[(1S)-2-({1-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]acetamide
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=O)[O:26]C(C)(C)C)[CH3:23])[CH2:16][CH2:15]4)=[N:11][C:10]=3[CH:32]=2)[CH2:3][CH2:2]1.Cl.[C:34](OCC)(=O)C>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:26])[CH3:34])[CH3:23])[CH2:16][CH2:15]4)=[N:11][C:10]=3[CH:32]=2)[CH2:3][CH2:2]1Participants
3
Procedure
To tert-butyl [(1S)-2-({1-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate (375 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 10 min. The reaction mixture was concentrated, the residue was purified by silica gel chromatography (NH, hexane/ethyl acetate), and the obtained solid was washed with diethyl ether-hexane to give the title compound (183 mg).
Workup
- concentrationconcentrated
- additionPyridine (5 mL) and acetic anhydride (5 mL) were added to the residue
- stirringthe mixture was stirred at room temperature for 10 min
- concentrationThe reaction mixture was concentrated
- customthe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)
- washthe obtained solid was washed with diethyl ether-hexane
Sources & evidence
- ORD record
- ord-c726a60951fb4468995aa261032524b6
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703758B2
Reaction notes
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