L-Alanine Isopropyl Ester

Uses

(S)-Isopropyl-2-aminopropanoate Hydrochloride, is a chemical reagent used in the synthesis of anti-HCV prodrugs based on imidazotriazine and pyrrolotriazine molecules.

Synthesis

Sulfoxide chloride (SOCl2, 29 mL, 400 mmol) was slowly added dropwise to a mixture of L-alanine hydrochloride (17.8 g, 200 mmol) suspended in isopropanol (700 mL) at 0 °C. Subsequently, the reaction mixture was continuously stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford the target product isopropyl (S)-2-aminopropionate (29.2 g, 87% yield).

References

[1] Patent: WO2015/56213, 2015, A1. Location in patent: Page/Page column 66
[2] Synthetic Communications, 2014, vol. 44, # 16, p. 2386 - 2392
[3] Journal of Molecular Structure, 2013, vol. 1041, p. 68 - 72
[4] Analytical Chemistry, 1991, vol. 63, # 4, p. 370 - 374
[5] Analytical Chemistry, 1997, vol. 69, # 5, p. 926 - 929