Isonitrosoketones**ChemotherapyBranch, Research Directorate, Army Chemical Center, Md.

Design and evaluation of switchable-hydrophilicity solvents

“…Ethyl acrylate (4.5 g, 0.045 mol) and sec-butylamine (6.6 g, 0.9 mol) were added to a round bottom flask and stirred for 24 h. Distillation afforded the pure product (7.0 g, 89% yield); bp: 65 °C (4 torr): 1 H NMR (500 MHz, CDCl 3 ) δ 0.77 (t, J = 7.4 Hz, 3H), 0.91 (d, J = 6.2 Hz, 3H), 1.14 (t, J = 7.2 Hz, 3H), 1.20 (m, 1H), 1.35 (m, 1H), 2.37 (t, J = 6.6 Hz, 2H), 2.44 (apparent sextet, J = 6.2 Hz, 1H), 2.75 (m, 2H), 4.02 (q, J = 7.2 Hz, 2H); 13 Ethyl 3-(tert-butylamino)propanoate. Using the same procedure as for ethyl 3-(sec-butylamino)propanoate, 1.9 g (0.019 mol) ethyl acrylate and 2.9 g (0.040 mol) tert-butylamine yielded 1.7 g product (51% yield); bp 62 °C (4 torr): 1 H NMR (300 MHz, CDCl 3 ) δ 1.05 (s, 9H), 1.21 (t, J = 7.1 Hz, 2H), 2.43 (t, J = 6.6 Hz, 2H), 2.77 (t, J = 6.6 Hz, 2H), 4.09 (q, J = 7.1 Hz, 2H); 13 C NMR (300 MHz, CDCl 3 ) δ 14.1, 28.9, 35.5, 38.0, 50.3, 60.2, 172.9; ν max (ATR) cm −1 3319 (N-H), 2964, 2868, 1731 (CvO), 1362, 1230, 1174, 1099, 102; m/z (EI), 173 (1), 158 (94), 144 (3), 130 (4), 116 (5), 112 (31), 86 (50), 70 (100), 58 (20), 57 (21), 56 (11) Ethyl 3-(isobutylamino)propanoate. Using the same procedure as for ethyl 3-(sec-butylamino)propanoate, 1.9 g (0.019 mol) ethyl acrylate and 3.1 g (0.042 mol) isobutylamine yielded 2.4 g product (73% yield); bp: 68 °C (4 torr): 1 H NMR (300 MHz, CDCl 3 ) δ 0.88 (d, J = 6.6 Hz, 6H), 1.24 (t, J = 7.1 Hz, 3H), 1.36 (broad, 1H) 1.71 (apparent nonet, J = 6.7 Hz, 1H), 2.40 (d, J = 6.8 Hz, 2H), 2.48 (t, J = 6.5 Hz, 2H), 2.84 (t, J = 6.5 Hz, 2H), 4.12 (q, J = 7.1 Hz, 2H); 13 (70), 116 (7), 86 (38), 84 (100), 70 (7), 57 (13)…”