Tetrahydrofuran → (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[CH2:11][C@@H:12](O)[CH2:13][CH3:14])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)C>[CH2:13]([C@H:12]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)[C:10](=[O:16])[CH2:11]1)[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension containing 200 mg (0.77 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-hydroxypentanoic acid amide produced in Example 2, triphenylphosphine (1,188 mg, 1.53 mmol), and tetrahydrofuran (1 mL), a tetrahydrofuran solution (1 mL) containing 309.8 mg (1.53 mmol) of diisopropyl azodicarboxylate was added dropwise at room temperature for 5 minutes. After stirring at the same temperature for further 1.5 hours, the solvent was removedby distillation under reduced pressure to obtain an oil. When diethyl ether cooled to 0° C. was added to the oil, a solid was precipitated, which was removed by vacuum filtration. The filtrate was concentrated under reduced pressure to obtain a white solid (342.0 mg). The reaction yield of the product was determined by the method described in Example 7 to be 30%.
Workup
- additionwas added dropwise at room temperature for 5 minutes
- distillationdistillation under reduced pressure
- customto obtain an oil
- additionwas added to the oil
- customa solid was precipitated
- customwhich was removed by vacuum filtration
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-59e44371ecce40d7bdfaf9288c0889ef
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223859B2
Reaction notes
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