[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:18]([NH2:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)C(C)C)(C)C.Cl>C(Cl)(Cl)Cl.ClCCl>[CH2:18]([NH:25][C:10]([C:7]1([C:4]2[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=2)[CH2:8][CH2:9]1)=[O:12])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]To a solution of 1-p-tolylcyclopropanecarboxylic acid (5.68 grams) in chloroform (10 mL) was added thionyl chloride (17.0 mmol, 1.26 mL). The resulting mixture was brought to reflux and was allowed to stir for 3 h. The mixture was cooled to room temperature and concentrated to give a yellow oil. The oil was dissolved in dichloromethane (5 mL) and added dropwise to a solution of 1-heptylamine (6.82 mmol, 1.01 mL) and N,N-diisopropylethylamine (6.82 mmol, 1.19 mL) dissolved in dichloromethane (10 mL) cooled to 0° C. The mixture was warmed to room temperature and was allowed to stir for 30 minutes. The solution was poured over 1 N HCl, and the aqueous layer was isolated and extracted with dichloromethane (3×). The organic layers were combined, washed with 2N HCl (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated to a yellow oil which solidified under high vacuum. The solid was crystallized from hexanes to give 1-p-tolyl-cyclopropanecarboxylic acid heptylamide as a white solid (1.0 g, 64%).
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