α-Aminoisobutyric acid methyl ester hydrochloride

White solid

2-amino-2-methylpropionic acid (10 g, 96.9 mmol) and methanol (330 ml) were charged. An ice bath was set and thionyl chloride (17.68 ml, 242.25 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60 oven so as to obtain methyl-2-amino-2-methylpropanoate hydrochloride (14.59 g, 94.9 mmol, 98 percent).[938] 2-amino-2-methylpropionic acid (10 g, 96.9 mmol) and methanol (330 ml) were charged. An ice bath was set and thionyl chloride (17.68 ml, 242.25 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-2-amino-2-methylpropanoate hydrochloride (14.59 g, 94.9 mmol, 98percent). [0514] To a suspension of 2-aminoisobutyric acid (25.0 g, 243 mmol) in methanol (300 ml.) was added thionyl chloride (27.0 ml_, 43.0 g, 365 mmol) and the reaction was heated at reflux for 12 hours. The resulting solution was concentrated and triturated with diethyl ether - tetrahydrofuran to yield the product as a white powder, 29.8 g (80 percent).Aminoisobutyric acid (29.80 g, 0.2890 mol) was suspended in MeOH (300 mE) and the suspension cooled to 0°C. (ice bath). Thionyl chloride (36.10 g, 0.3034 mol) was added dropwise over 15 mm. The ice bath was removed and the reaction mixture stirred at 60°C. for 4 h. The oil bath was then removed and stirring continued at room temperature for another 22 h. The solvent and excess thionyl chloride were evaporated affording a white solid with a strong sulfur smell. Methanol (5x 150 mE) was added and evaporated. The residue was dissolved in MeOH (120 mE), precipitated by addition of Et20 (720 mE) and collected by filtration under suction affording the title compound as a white solid (35.12 g, 79percent), with spectral characteristics in accordance with literature data’; ‘H NMR (200 MHz, DMSO-d5) ö 8.87 (br s, 3H, NH3), 3.72 (s, 3H, OCH3), 1.48 (s, 6H, CH3); ‘3CNMR(75 MHz, DMSO-d5) ö 172.0, 55.8, 53.1, 23.3; HRMS (mlz): M calcd. for C5, H, 2N02, 118.0868. found, 118.0871; Anal. Calcd. for C5H, 2C1N02: C, 39.10; H, 7.87; N, 9.12. Found:C, 38.9; H, 7.8; N, 9.0.

Molecular Weight:153.61
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:153.0556563
Monoisotopic Mass:153.0556563
Topological Polar Surface Area:52.3
Heavy Atom Count:9
Complexity:98.6
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes