反应详情

温度

0 °C

A solution of 2-tert-butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid (5.0 g, 12.8 mmol) in DMF (50 mL) was treated with K2CO3 (2.2 g, 15.4 mmol). After stirring for 15 min, the solution was cooled to 0° C. and treated with iodomethane (1.0 mL, 15.4 mmol). After the addition was complete, the reaction mixture was stirred at room temperature for another 16 h, filtered and the resulting solid was washed with ethyl acetate (200 mL). The filtrate was washed successively with 5% aq HCl, sat. aq NaCl, dried over MgSO4 and concented. Purification by flash column chromatography (5% ethyl acetate in heptane) provided the desired product (5.74 g, 98%) as an oil. 1H NMR (CDCl3), δ 7.61 (d, J=9 Hz, 2 H), 7.74 (d, J=9, 2 H), 4.97 (d, J=7 Hz, 1 H), 4.56 (m, 1 H), 3.73 (s, 3 H), 3.02 (ddd, J=7, 7, 12 Hz, 2 H), 1.47 (s, 9H).

1. additionAfter the addition
2. stirringthe reaction mixture was stirred at room temperature for another 16 h
3. filtrationfiltered
4. washthe resulting solid was washed with ethyl acetate (200 mL)
5. washThe filtrate was washed successively with 5% aq HCl, sat. aq NaCl
6. dry with materialdried over MgSO4
7. customPurification by flash column chromatography (5% ethyl acetate in heptane)