Triethylamine → [3-(4-Bromo-phenyl)-5-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[C:12](C(O)=O)=[C:11]([CH3:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C@H:48]([OH:50])[CH3:49]>C1(C)C=CC=CC=1>[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C@H:48]([O:50][C:22](=[O:31])[NH:19][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N:9][O:10][C:11]=1[CH3:16])[CH3:49]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-(4-bromophenyl)-5-methylisoxazole-4-carboxylic acid (0.100 g, 0.35 mmol) in toluene (3 mL) was added triethylamine (0.054 mL, 0.39 mmol) and diphenylphosphoryl azide (0.084 mL, 0.39 mmol), followed by (R)-1-(2-fluoro-phenyl)-ethanol (0.055 g, 0.39 mmol), and the reaction was stirred at 80° C. for 1 hour. Once no starting material was seen by analytical LCMS, standard aqueous work-up was performed. The organic layer was treated with silica gel, and the mixture was concentrated and purified by silica gel chromatography to give the title compound.
Workup
- additionThe organic layer was treated with silica gel
- concentrationthe mixture was concentrated
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-7eaf8b10f6bf49cf870e164d6581df2c
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592402B2
Reaction notes
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