Hydrogen chloride-ethyl acetate → N-((2S)-1-((4-chloro-5-nitropyridin-2-yl)oxy)propan-2-yl)acetamide
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])OC(C)(C)C)[CH3:14])[CH:3]=1.Cl.[C:24](OCC)(=O)C>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[CH3:24])[CH3:14])[CH:3]=1Participants
3
Procedure
To tert-butyl ((2S)-1-((4-chloro-5-nitropyridin-2-yl)oxy)propan-2-yl)carbamate (1.35 g) was added 4 M hydrogen chloride/ethyl acetate (5 mL), and the mixture was stirred at room temperature for 10 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 mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.00 g). 1H NMR (300 MHz, CDCl3) δ 1.27 (3H, d, J=6.4 Hz), 1.98 (3H, s), 4.33-4.55 (3H, m), 5.65 (1H, d, J=6.1 Hz), 6.94 (1H, s), 8.86 (1H, s).
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 mixture was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-cabfc37f95f3440b84efd2a24c3196f8
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133129B2
Reaction notes
Loading…