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To a suspensionof sodium hydride (60 percent, 18.4 g, 768.47 mmol) in toluene (350 mL) at 0 °C was added portion wise Intermediate 11 (120 g, 591.13 mmol). After stirring for 5 h at this temperature, to the mixture was added drop wise ethyl acrylate (76.8 g, 768.47 mmol). After additional stirring for 2 h at rt, the reaction was quenched with water (200 mL) carefully and extracted with EtOAc (600 mL X 2). The combined extract was dried over anhydrous sodium sulfate, concentrated to afford crude Intermediate 12 (50 g, 33percent yield, pale brown liquid).JH NMR (400 MHz, CDCb)
STR65 Ethyl 2-(tert-butoxycarbonylamino)acetate (4.17 g, 20.52 mmol) was dissolved in tetrahydrofuran (60 ml). The solution was cooled to -78 C. A 22% solution of methyl magensium chloride in toluene/tetrahydrofuran (purchased from Chemmetallgesellschaft, 27.1 ml, 67.72 mmol) was added dropwise. The reaction mixture was stirred for 1.5 h at -78 C. and then warmed to room temperature. A 10% aqueous solution of ammonium chloride (200 ml) was added dropwise. The phases were separated. The aqueous phase was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with saturated sodium hydrogen carbonate solution (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (110 g), using ethyl acetate/heptane (1:1) as eluent, to give 1.31 g of 2-hydroxy-2-methylpropylcarbamic acid tert-butyl ester. 1 H-NMR (CDCl3): d 1.21 (s, 6 H); 1.45 (s, 9 H); 1.34 (d, 2 H); 5.00 (br, 1H).
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