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With sodium hydroxide In tetrahydrofuran; water at 20 - 30℃; for 17 h;
To a mixture of 3-amino-3-cyclopropylpropanoic acid (146 g, 1.13 mol), water (300 mL), and tetrahydrofuran (1 L) was added an aqueous solution of sodium hydroxide (95 g, 2.37 mol; 200 mL of water) while maintaining the internal temperature below 30 °C. A solution of di-t-butyl dicarbonate (271.7 g, 1.24 mol) in tetrahydrofuran (250 mL) was added to the reaction via addition funnel while maintaining the internal temperature below 30 °C with the aid of a water bath. The reaction was stirred at ambient temperature for a period of 17 h, at which point LCMS analysis indicated that the starting material had been consumed. The reaction mixture was quenched by portionwise addition of oxalic acid to a pH of 4 and the precipitated salts removed by filtration. The salts were rinsed with ethyl acetate (slurry-wash: 1 x 500 mL; displacement wash: 1 x 500 mL) and the phases were split. The aqueous layer was extracted with ethyl acetate (2 x 250 mL), the combined organic layers washed with brine (1 x 400 mL), dried over sodium sulfate, filtered and the majority of the solvent removed to provide a thick slurry. The product slurry was diluted with hexanes (500 mL) and cooled to 0 °C prior to filtration. The cake was washed with cold hexanes (displacement wash: 1 x 300 mL) and dried under vacuum to afford the desired compound (236.3 g, 91.3percent yield) as a white solid. mp: 104-106 °C.
With sodium hydroxide; In tetrahydrofuran; water; at 20 - 30℃; for 17.0h;
To a mixture of 3-amino-3-cyclopropylpropanoic acid (146 g, 1.13 mol), water (300 mL), and tetrahydrofuran (1 L) was added an aqueous solution of sodium hydroxide (95 g, 2.37 mol; 200 mL of water) while maintaining the internal temperature below 30 C. A solution of di-t-butyl dicarbonate (271.7 g, 1.24 mol) in tetrahydrofuran (250 mL) was added to the reaction via addition funnel while maintaining the internal temperature below 30 C with the aid of a water bath. The reaction was stirred at ambient temperature for a period of 17 h, at which point LCMS analysis indicated that the starting material had been consumed. The reaction mixture was quenched by portionwise addition of oxalic acid to a pH of 4 and the precipitated salts removed by filtration. The salts were rinsed with ethyl acetate (slurry-wash: 1 x 500 mL; displacement wash: 1 x 500 mL) and the phases were split. The aqueous layer was extracted with ethyl acetate (2 x 250 mL), the combined organic layers washed with brine (1 x 400 mL), dried over sodium sulfate, filtered and the majority of the solvent removed to provide a thick slurry. The product slurry was diluted with hexanes (500 mL) and cooled to 0 C prior to filtration. The cake was washed with cold hexanes (displacement wash: 1 x 300 mL) and dried under vacuum to afford the desired compound (236.3 g, 91.3% yield) as a white solid. mp: 104-106 C.
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