反应详情

In a round-bottomed flask were combined Boc-D-alanine (500 mg, 2.64 mmol), azetidine-3-carbonitrile hydrochloride (376 mg, 3.17 mmol), HOBT (445 mg, 2.91 mmol) and HATU (1.11 g, 2.91 mmol). Then added DMF (5 mL) followed by N,N-diisopropylethylamine (1.38 mL, 7.93 mmol). The yellow reaction mixture was stirred at room temperature for 3 h then quenched with water and extracted with EtOAc (3×). The combined organics were washed with water (3×) dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes) to afford 493 mg (74%) of [(R)-2-(3-cyanoazetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester as a white solid.

1. customIn a round-bottomed flask were combined
2. customthen quenched with water
3. extractionextracted with EtOAc (3×)
4. washThe combined organics were washed with water (3×)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes)