反应详情

To a solution of cyclopropyl-2-(2-nitro-benzenesulfonylamino)-propionic acid (7.74 mmol) in DMF (10 mL) are added 2-(S)-amino-3-naphthalen-2-yl-propionic acid methyl ester (3.1 g, 11.7 mmol), N-methylmorpholine (4.67 g, 46.27 mmol), 1-hydroxybenzotriazole (17.76 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.93 g, 10.07 mmol) consecutively. The resulting mixture is stirred for 4 hours, quenched with aqueous NH4Cl and extracted with ethyl acetate. The combined extracts are dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified over silica gel (hexanes/ethyl acetate, 1:1) to afford 3.46 g (85% yield) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.04 (dd, J=7.7, 1.4 Hz, 1H), 7.42–7.68 (m, 9H), 7.24 (dd, J=8.4, 1.5 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 6.20 (d, J=6.9 Hz, 1H), 4.84–4.96 (m, 1H), 3.98–4.07 (m, 1H), 3.71 (s, 3H), 3.29 (dd, J=14.0, 5.6 Hz, 1H), 3.14 (dd, J=14.0, 7.4 Hz, 1H), 1.62–1.72 (m, 1H), 1.23–1.42 (m, 1H), 0.02–0.40 (m, 3H), −0.14–0.02(, 2H); 13C NMR (75 MHz, CDCl3) δ 171.74, 170.45, 147.91, 134.02, 133.73, 133.61, 133.18, 132.70, 131.07, 128.55, 128.32, 127.89, 127.41, 126.54, 126.12, 125.76, 58.59, 53.56, 52.74, 38.34, 37.55, 6.86, 4.38; MS (ESMS) m/z 526.1 (M+H)+.

1. customquenched with aqueous NH4Cl
2. extractionextracted with ethyl acetate
3. dry with materialThe combined extracts are dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue is purified over silica gel (hexanes/ethyl acetate, 1:1)