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ChemicalBook CAS DataBase List ethyl 2-(5-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate

ethyl 2-(5-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate synthesis

5synthesis methods
-

Yield:921940-82-1 85%

Reaction Conditions:

in 1,4-dioxane at 18 - 25; for 18 h;Heating / reflux;

Steps:

1.4

To a stirred solution of ethyl (5-aminopyridin-2-yl)acetate (2.80 g, 15.6 mmol, step 3 of Example 1 ) in 1 ,4-dioxane (22 mL) was added di-terf-butyl dicarbonate (4.08 g, 18.7 mmol) at room temperature. The mixture was refluxed for 18 h. After cooling, the mixture was quenched with water (200 mL), extracted with ethyl acetate (60 mL x 5). The combined organic layer was washed with water (60 mL x 5), brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (2:1 ) to give 3.72 g (85%) of the title compound as a yellow crystal. 1H NMR (CDCI3) δ 8.36 (1 H, d, J = 2.6 Hz), 8.03-7.91 (1 H, m), 7.24 (1 H, d, J = 8.4 Hz), 6.67 (1 H, br.), 4.18 (2 H, q, J = 7.1 Hz), 3.79 (2 H, s), 1.52 (9 H, s), 1.25 (3 H, t, J = 7.1 Hz).

References:

WO2007/10390,2007,A1 Location in patent:Page/Page column 25