Sodium Hydroxide → 2-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester

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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).

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