Ethyl sarcosinate hydrochloride synthesis
- Product Name:Ethyl sarcosinate hydrochloride
- CAS Number:52605-49-9
- Molecular formula:C5H12ClNO2
- Molecular Weight:153.61
107-97-1
52605-49-9
Thiophenecarbonyl chloride (65 mL, 900 mmol) was added dropwise to a solution of sarcosine (20.0 g, 224 mmol) in ethanol (250 mL) cooled in an ice-water bath under stirring conditions, and the reaction temperature was maintained at about -10°C. After the dropwise addition was completed, the reaction mixture was gently heated at 55°C overnight until the solution became clear. Upon completion of the reaction, the solvent and residual thionyl chloride were removed by distillation under reduced pressure. The resulting solid residue was washed with ether (3 x 50 mL) and subsequently dried well under vacuum to afford ethyl sarcosinate hydrochloride (33.5 g, 218 mmol) in white powder form in 97% yield. The product could be used in subsequent steps without further purification. The product was characterized as follows: melting point 126°C (literature value 125-127°C); IR (ATR) ν cm?1 2970-2440, 1742, 1229; 1H NMR (CDCl?, 400 MHz) δ 9.64 (br.s, 2H, NH?), 4.24 (q, 2H, 3J = 7.1 Hz, CH?CH?), 3.84 (t, 2H, 3J = 7.1 Hz, CH?CH?), 4.24 (q, 2H, 3J = 7.1 Hz, CH? 3.84 (t, 2H, 3J = 5.7 Hz, NH?CH?), 2.80 (t, 3H, 3J = 5.2 Hz, NH?CH?), 1.26 (t, 3H, 3J = 7.1 Hz, CH?CH?); 13C NMR (CDCl?, 101 MHz) δ 166.18 (CO?), 62.62 (CH?CH?), 48.94 (NH?CH?), 33.34 (NH?CH?), 14.03 (CH?CH?).
107-97-1
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52605-49-9
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$6.00/10g
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]