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

関与物質

反応手順

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), prepartive 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): 9.68δ (s, 1H, NH), 6.50δ (t, 1H, ##STR74## 2.83δ (t, 1H, 1.97δ (d, ##STR75## 0.87δ (t, 3H, CH3).

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