Hydrochloric Acid → HCID 57867417, compound
Reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[C:11]([C:12]2[O:16][N:15]=[C:14]([C:17](OCC)=[O:18])[CH:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:4].[BH4-].[Na+].Cl.[OH-].[Na+]>O.O1CCCC1.C(O)C>[OH:18][CH2:17][C:14]1[CH:13]=[C:12]([C:11]2[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:22])([CH3:1])[CH3:23])=[N:7][CH:8]=[CH:9][CH:10]=2)[O:16][N:15]=1Participants
Procedure
To a mixture of ethyl 5-{2-[(2,2-dimethylpropanoyl)amino]pyridin-3-yl}isoxazol-3-carboxylate (111 g, 350 mmol), ethanol (110 mL) and tetrahydrofuran (350 mL) was added sodium borohydride (13.2 g, 350 mmol) at room temperature, which was stirred at room temperature for 6 hours. To the reaction mixture were added water (350 mL) and 5N hydrochloric acid (90 mL), which was stirred at room temperature for 30 minutes, 5N aqueous sodium hydroxide (110 mL) was added thereto, the solution was extracted with a mixture of ethyl acetate and tetrahydrofuran, and the organic layer was washed with water and saturated sodium chloride water. The solvent was evaporated under a reduced pressure to obtain the title compound (83.8 g) as a yellow solid, partially contaminated with [5-(2-aminopyridin-3-yl)isoxazol-3-yl]methanol.
Workup
- stirringwas stirred at room temperature for 30 minutes
- extractionthe solution was extracted with a mixture of ethyl acetate and tetrahydrofuran
- washthe organic layer was washed with water and saturated sodium chloride water
- customThe solvent was evaporated under a reduced pressure
Sources & evidence
- ORD record
- ord-f90d28d2db164da880989ed41a823934
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188119B2
Reaction notes
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