DiMethyl 3-aMinopentanedioate acetate synthesis

Yield:-

Reaction Conditions:

in tert-butyl methyl ether at 15;Cooling with ice;

Steps:

A solution of dimethyl 3-aminopentanedioate (568 g, 3.24 mol) in terf-butyl methyl ether (2.3 L) was cooled in an ice bath and glacial acetic acid (195, 3.24 mol) was added dropwise while maintaining the reaction temp at ca. 15°C. The resulting mixture was seeded with a small quantity of the desired crystalline product and stirred for 90 min with cooling to 5°C. The resulting precipitate was collected by filtration and washed with 1 :1 terf-butyl methyl ether/heptane. The filter cake was dried under vacuum to afford the acetic acid salt of dimethyl 3-aminopentanedioate as an off-white solid (640 g): ¹ H NMR (DMSO-d₆) δ ppm 5.30 (br s, 3 H), 3.56 (s, 6 H), 3.36 (m, 1 H), 2.44 (dd, J=16, J=5, 2 H), 2.31 (dd, J=16, J=8, 2 H), 1 .86 (s, 3 H).

References:

GLAXOSMITHKLINE LLC;AQUINO, Christopher Joseph;COLLINS, Jon Loren;COWAN, David John;WU, Yulin WO2011/137135, 2011, A1 Location in patent:Page/Page column 60-61