Yield:52605-49-9 97%

Reaction Conditions:

with thionyl chloride in ethanol at -10 - 55;

Steps:

1.1 4.1.1.1. Ethyl N-methylglycinate hydrochloride salt (2).

Thionyle chloride (65?mL, 900?mmol) was added dropwise under stirring to a solution of sarcosine (1) (20.0?g, 224?mmol) in EtOH (250?mL) cooled in an ice-water bath, while maintaining temperature around -10?°C. Then the reaction mixture was gently heated at 55?°C overnight until the mixture became clear. Solvent and traces of thionyl chloride were removed by evaporation under reduced pressure and the solid residue was washed with Et₂O (3?*?50?mL). The remaining solid was well dried under vacuum to afford compound 2 (33.5?g, 218?mmol) as a white powder, which was used in the next step without further purification. Yield 97%; mp 126?°C (Lit [52]. mp 125-127 C); IR (ATR) n cm1 2970-2440, 1742, 1229; 1HNMR (CDCl3, 400 MHz) δ 9.64 (br.s, 2H, NH2), 4.24 (q, 2H,3J 7.1 Hz, CH2CH3), 3.84 (t, 2H, 3J 5.7 Hz, NH2CH2), 2.80 (t, 3H,3J 5.2 Hz, NH2CH3), 1.26 (t, 3H, 3J 7.1 Hz, CH2CH3); 13C NMR(CDCl3, 101 MHz) δ 166.18 (CO2), 62.62 (CH2CH3), 48.94 (NH2CH2),33.34 (NH2CH3), 14.03 (CH2CH3).

References:

Ghedira, Donia;Voissière, Aurélien;Peyrode, Caroline;Kraiem, Jamil;Gerard, Yvain;Maubert, Elise;Vivier, Magali;Miot-Noirault, Elisabeth;Chezal, Jean-Michel;Farhat, Farhat;Weber, Valérie [European Journal of Medicinal Chemistry,2018,vol. 158,p. 51 - 67]