Triethylamine → [5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl Ester
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][C:3]=1[CH3:17].C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([OH:51])[CH3:50]>C1(C)C=CC=CC=1>[F:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C@H:49]([O:51][C:23](=[O:32])[NH:20][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:17])[CH:4]=1)[CH3:50]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1.78 g, 6.0 mmol) was dissolved in toluene (50 mL). Triethylamine (0.92 mL, 6.6 mmol) was added, followed by diphenylphosphoryl azide (1.43 mL, 6.6 mmol), and the mixture was stirred for 10 minutes. (R)-1-(2-Fluoro-phenyl)-ethanol (0.924 g, 6.6 mmol) was added, and the reaction was stirred at 85° C. for 3 hours, and then overnight at room temperature. The mixture was concentrated, and the residue was diluted with dichloromethane and purified by silica gel chromatography to give the title compound.
Workup
- stirringthe reaction was stirred at 85° C. for 3 hours
- customovernight
- customat room temperature
- concentrationThe mixture was concentrated
- additionthe residue was diluted with dichloromethane
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-f9856a0c813e4a3c9e8b2b9c62c56303
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440707B2
Reaction notes
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