Sodium Hydroxide → 2-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester
Reaction equation
S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].[C:42]([O:46][C:47](=[O:63])[CH2:48][N:49]=[C:50]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([CH3:45])([CH3:44])[CH3:43].Br[CH2:65][C:66]1[CH:71]=[C:70]([O:72][CH3:73])[CH:69]=[CH:68][C:67]=1[F:74]>ClCCl.CCOCC>[C:42]([O:46][C:47](=[O:63])[CH:48]([N:49]=[C:50]([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[CH2:65][C:66]1[CH:71]=[C:70]([O:72][CH3:73])[CH:69]=[CH:68][C:67]=1[F:74])([CH3:45])([CH3:43])[CH3:44]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Tetrabutylammonium sulfate (156.2 mg, 0.46 mmol) was added to a two-phase mixture consisting of 10% NaOH (2.5 mL), t-butylglycinate Schiff base 3 (142.7 mg, 0.48 mmol), and 2-fluoro-5-methoxybenzyl bromide 35 (100 mg, 0.46 mmol) in dichloromethane (2.0 mL). After 5 h of vigorous stirring at ambient temperature, the reaction mixture was diluted with ether (10 mL) and the layers were separated. The organic layer was washed with water (3×3.0 mL), dried over sodium sulfate, filtered, and evaporated in vacuo. A crude yellow oil of 40 was obtained in 90% yield. The pure product 40 was made as a residue in 83% (149 mg).
Workup
- customthe layers were separated
- washThe organic layer was washed with water (3×3.0 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-fac0808567ce480985310753640a33eb
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115766B2
Reaction notes
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