反应详情

3-({5-[3-methyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-butylamino]-pyrimidine-2-carbonyl}-amino)-propionic acid ethyl ester Peak 1 (286.4 mg, 0.542 mmol) was dissolved in tetrahydrofuran (3 mL) and methanol (1 mL), and 1.0 M NaOH (2 mL, 2 mmol) was added. This was stirred at room temperature for 10 min. The reaction brought to pH 3 with 1 N HCl. This was extracted twice with ethyl acetate. The combined organics were dried over MgSO4 and concentrated in vacuo to give an oil. The material was triturated with four portions of diethylether to give one enantiomer of 3-({5-[3-methyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-butylamino]-pyrimidine-2-carbonyl}-amino)-propionic acid (266 mg, 97%) as a white solid. 1H NMR (400 MHz, DMSO-d6, δ): 12.21 (br. s., 1 H) 8.39 (t, J=6.0 Hz, 1 H) 8.16 (s, 2 H) 7.83-7.91 (m, 2 H) 7.75-7.81 (m, 2 H) 7.70 (d, J=8.2 Hz, 2 H) 7.54 (d, J=8.2 Hz, 2 H) 7.27 (d, J=7.6 Hz, 1 H) 4.60-4.72 (m, 1 H) 3.36-3.46 (m, 2 H) 2.44 (t, J=6.9 Hz, 2 H) 1.74-1.85 (m, 1 H) 1.67 (m, 1 H) 1.51-1.60 (m, 1 H) 0.98 (d, J=6.4 Hz, 3 H) 0.92 (d, J=6.4 Hz, 3 H); MS (M+1): 501.6.

1. extractionThis was extracted twice with ethyl acetate
2. dry with materialThe combined organics were dried over MgSO4
3. concentrationconcentrated in vacuo
4. customto give an oil
5. customThe material was triturated with four portions of diethylether