2-Oxooctanoic acid → Z-2-(2,2-dichlorocyclopropanecarboxamido)-2-octenoic acid

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A mixture of 1.19 g (7.5 mmoles) of 2-ketooctanoic acid, 0.77 g (5.0 mmoles) of 2,2-dichlorocyclopropanecarboxamide, and 5 ml toluene were reacted using the same procedure as in the previous example. The crude product (537 mg) was purified by conversion to the methyl ester (BF3 /CH3OH), preparative TLC (silica gel G, 4:1 hexane-EtOAc) and saponification of the pure Z-methyl ester (0.3M LiOH/CH3OH) to give 88 mg of Z-2-(2,2-dichlorocyclopropanecarboxamido)-2-octenoic acid as a partially crystalline gum. NMR spectrum (DMSO-d6): δ9.68 (s, 1H, NH), 6.50 δ (t, 1H, ##STR72## 2.83δ (t, 1H, ##STR73## 1.97 δ (d, 2H ##STR74## 0.87 δ (t, 3H, CH3).

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