Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate → methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate

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Reaction Steps

To a 1.6 M solution of pent-4-enohydrazide (from Step 2) in dioxane, 1 eq. of methyl N-(oxomethylene)-L-valinate, (prepared as described in J. Het. Chem. 1990, 739) was added. After sting at RT for 3 h, volatiles were removed in vacuo, to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 9.55 (d, J 2.1, 1H), 7.86 (d, J 2.2, 1H), 6.48 (d, J 8.1, 1H), 5.86-5.76 (m, 1H), 5.04 (dd, J 17.2, 1.5, 1H), 4.96 (d, J 18.2, 10.3, 1H), 4.09 (dd, J 8.7, 5.7, 1H), 3.64 (s, 3H), 2.32-2.24 (m, 2H), 2.22-2.15 (m, 2H), 2.08-1.90 (m, 1H), 0.94 (d, J 3.9, 3H), 0.92 (d, J 3.9, 3H). MS (ES+) C12H21N3O4 requires: 271 found: 272 (M+H+).

Provenance & Evidence