Hydrogen chloride-ethyl acetate → N-((2S)-1-((2-(4-(benzyloxy)-3-fluorophenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27]C(=O)OC(C)(C)C)[CH3:26])[N:20]=[CH:19][C:18]=3[N:35]=2)=[CH:11][C:10]=1[F:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:38](OCC)(=[O:40])[CH3:39]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27][C:38](=[O:40])[CH3:39])[CH3:26])[N:20]=[CH:19][C:18]=3[N:35]=2)=[CH:11][C:10]=1[F:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Reactant 2
Product 1
Procedure
To tert-butyl ((2S)-1-((2-(4-(benzyloxy)-3-fluorophenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate (1.35 g) was added 4 M hydrogen chloride/ethyl acetate (20 mL), and the mixture was stirred at room temperature for 10 min, and then concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in THF and methanol, and the solution was subjected to NH silica gel column chromatography (ethyl acetate). The solvent was evaporated, and the obtained solid was washed with ethyl acetate/hexane to give the title compound (1.00 g).
Workup
- concentrationconcentrated
- additionTo the residue were added pyridine (10 mL) and acetic anhydride (10 mL)
- stirringthe mixture was stirred at room temperature for 15 min
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in THF
- customThe solvent was evaporated
- washthe obtained solid was washed with ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-4b1839d67e7f42439defa70afdb97e82
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133129B2
Reaction notes
Loading…