Benzylamine → N-Benzyl-[4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl]acetamide

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Reaction Steps

Treatment of (4-(4-methoxyphenylthio)-2-oxoazetidin-1yl)acetic acid with benzylamine under the conditions described in Example 86 gave the title compound as a colourless oil, 74% yield. 1H NMR δ (CDCl3) 2.80, 2.86 (1H, dd, J=2.3, 15.2 Hz, H3), 3.29, 3.35 (1H, dd, J=5, 15.2 Hz, H3), 3.79 (3H, s, OCH3), 3.85, 4.05 (each 1H, d, J=16.7 Hz, NCH2), 4.43 (2H, d, J=5.7 Hz, NHCH2), 4.97 (1H, m, H4) 6.5 (1H, m, NH), 6.83 (2H, d, J=8.6 Hz, 4-OCH3Ph-H), 7.24-7.35 (7H, m, Ph-H, 4-OCH3Ph-H). ν c=o 1775 cm-1. Found: C, 64.0 H, 5.8; N, 8.1%. C19H20N2O3S requires: C, 64.0; H, 5.7 N, 7.9%

Provenance & Evidence