反应详情

A solution of 6-phenylhexylamine (Morse M. A. et al., Cancer Research, 1991, 1846), (1.4 g, 8 mmol) in DMF (50 ml) was added to DCC (1.6 g, 8 mmol), hydroxybenzotriazole (1.0 g, 8 mmol) and (4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl)acetic acid (2.1 g, 8 mmol) and the mixture stirred for 2 hours at room temperature. Ethyl acetate (250 ml) was added, the precipitate filtered, the filtrate washed with dil NaHCO3, water (x2), dried (MgSO4) and evaporated to an oil which was purified by flash chromatography on silica gel using hexane/ethyl acetate (1:3). Evaporation of the appropriate fractions gave the product as a colourless oil, 77% yield. 1H NMR δ (CDCl3) 1.34-1.47 (10H, m, (CH2)5), 2.59 (2H, t, J=7.7 Hz, CH2), 2.83 (1H, dd, J=2.2, 15 Hz, H3a), 3.18-3.36 (3H, m, CH2H3b), 3.78 (3H, s, OCH3), 3.80, 3.99 (each 1H, d, J=15 Hz, NCH2), 4.95 (1H, m, H4), 6.23 (1H, bt, NH), 6.87 (2H, d, J=6.8 Hz, 2, 6 Ph--H), 7.14-7.39 (7H, m, 3, 5 Ph--H, Ph--H).

1. filtrationthe precipitate filtered
2. washthe filtrate washed with dil NaHCO3, water (x2)
3. dry with materialdried (MgSO4)
4. customevaporated to an oil which
5. customwas purified by flash chromatography on silica gel
6. customEvaporation of the appropriate fractions