Triethylamine → dimethyl N-(2-fluoro-4-iodobenzoyl)-L-glutamate

Participants

Reaction Steps

To 20 mL of benzene are added 2.0 g (0.00752 mol) of 2-fluoro4-iodobenzoic acid, followed by 2.3 mL (320 mmol) of thionyl chloride and several drops of dimethylformamide. The mixture is heated at reflux of 3.5 hours. The solvent is then removed in vacuo and the residue pumped dry. The resulting acid chloride is redissolved in 10 ml of methylene chloride, and added dropwise to cooled mixture of 1.67 g (7.89 mmol) of L-glutamic acid dimethyl ester hydrochloride, 5 mg of 4-dimethylaminopyridine, and 2.2 mL (15.8 mmol) of triethylamine in 30 mL of methylene chloride. After the addition, the reaction stirred at room temperature for 18 hours. The reaction mixture is then diluted with additional methylene chloride, washed with 1N hydrochloric acid, water and 5% sodium bicarbonate and dried over sodium sulfate. The solvent is removed in vacuo to give 2.34 g (74%) of dimethyl N-(2-fluoro-4-iodobenzoyl)-L-glutamate as a white solid m.p. 94°-96° C.; IR (KBr, cm-1)=1159, 1177, 1194, 1208, 1229, 1398, 1437, 1477, 1537, 1601, 1642, 1728, 1739, 1756, 3326.

Provenance & Evidence