Triethylamine → [5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)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][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.[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([OH:46])[CH3:45]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([O:46][C:22](=[O:31])[NH:19][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:45]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (5.764 g, 20.4 mmol) in toluene (200 mL) was added triethylamine (3.13 mL, 22.4 mmol) and diphenylphosphoryl azide (4.42 mL, 20.4 mmol), and the mixture was stirred for 5 minutes at room temperature. 2-Chloro-alpha-methylbenzyl alcohol (3.2 g, 22.4 mol) was added, and the reaction was stirred at 80° C. for 2 hours. The mixture was diluted with EtOAc (200 mL) and extracted with EtOAc. The combined organic layers were washed twice with water and once with brine, and the combined aqueous layers were back-extracted with EtOAc. The combined organic layers were concentrated, and the residue was purified by silica gel chromatography to give [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-chloro-phenyl)-ethyl ester.
Workup
- stirringthe reaction was stirred at 80° C. for 2 hours
- extractionextracted with EtOAc
- washThe combined organic layers were washed twice with water and once with brine
- extractionthe combined aqueous layers were back-extracted with EtOAc
- concentrationThe combined organic layers were concentrated
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-084d224c1a004ba4ada8bbf63d43dc37
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440707B2
Reaction notes
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