反应详情

温度

0 °C

1.2 mL of Trifluoromethanesulfonic anhydride (7.1 mmol) is added slowly dropwise to a solution of 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (2.70 g, 6.4 mmol) and 0.7 mL (8.7 mmol) of pyridine in 20 mL of CH2Cl2 at 0° C., and the solution is stirred at 0° C. for 1 hour. The reaction mixture is then partitioned between water and CH2Cl2. The organic phase is separated and washed with saturated aqueous NaHCO3 solution, dried over MgSO4, filtered, and concentrated to yield 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester as a tan solid; 1H NMR (250 MHz, CDCl3) δ7.25 (d, 2 H), 7.17 (d, 2 H), 4.80 (q, 1 H), 4.75 (s, 1 H), 4.10 (two quarters, 2 H), 3.12 (ABX m, 2 H), 2.00-2.20 (m, 2 H), 1.60-2.00 (m, 6 H), 1.40 (s, 9 H), 1.18 (t, 3 H).

1. customThe reaction mixture is then partitioned between water and CH2Cl2
2. customThe organic phase is separated
3. washwashed with saturated aqueous NaHCO3 solution
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated