[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH2:25]([NH:32][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
To a solution of 10-phenyldecanoic acid (1.101 g, 4.43 mmol) in 20 mL of CH2Cl2 at room temperature was added oxalyl chloride (1.41 g, 11.08 mmol) and 1 drop of DMF, and the reaction mixture was stirred for 1 hour under nitrogen. The CH2Cl2 and excess oxalyl chloride were evaporated. The reaction was redissolved in CH2Cl2 and benzylamine (1.42 g, 13.3 mmol) and 2 mL of saturated aqueous NaHCO3 were added and the reaction stirred for 12 hours. The reaction was taken up in EtOAc and washed with 1N HCl×2, followed by saturated aqueous NaCl, and evaporated to give 1.462 g (98%) of an oil that was used without further purification. 1H NMR (CDCl3, 300 MHz) δ 1.30 (m, 10H), 1.55-1.72 (m, 4H), 2.20 (t, 2H), 2.59 (t, 2H), 4.45 (d, 2H), 5.68 (bs, 1H), 7.12-7.38 (m, 10H). MS (DCl--NH3) m/e (M+H)+ 338.
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