Ammonia → HCID 22013876, compound
Reaction equation
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:14][CH:13]=1)[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[NH3:33].[OH-].[Na+]>CO.O1CCCC1>[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:24][C:25]=2[CH3:26])=[CH:16][CH:17]=1)[C:6]([NH2:33])=[O:7])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 2-acetylamino-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (1.63 g, 3.73 mmol) obtained in Example 33 was dissolved in methanol-tetrahydrofuran (1:1, 50 ml). 28% Aqueous ammonia (20 ml) was added and the mixture was stirred at room temperature for 2 days. Thereto was added 1N aqueous sodium hydroxide solution (30 ml) and the mixture was stirred for 1 hr. The solvent was evaporated under reduced pressure and the obtained residue was partitioned between tetrahydrofuran-ethyl acetate (1:1, 100 ml) and water (50 ml). The organic layer was washed with saturated brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue (1.00 g) was washed with hot methanol to give the title compound (560 mg, yield 36%) as a white solid.
Workup
- stirringthe mixture was stirred for 1 hr
- customThe solvent was evaporated under reduced pressure
- customthe obtained residue was partitioned between tetrahydrofuran-ethyl acetate (1:1, 100 ml) and water (50 ml)
- washThe organic layer was washed with saturated brine (50 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- washThe residue (1.00 g) was washed with hot methanol
Sources & evidence
- ORD record
- ord-919bbd78ee9c496db74036e055e27299
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204277B1
Reaction notes
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