H-ALA-NHME HCL

H-ALA-NHME HCL Property

Melting point:

218-220 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

H-ALA-NHME HCL Chemical Properties,Usage,Production

Chemical Properties

White powder or solid

Uses

H-Ala-NHMe HCl

Synthesis

The general procedure for the synthesis of (S)-2-amino-N-methylpropionamide hydrochloride from L-alanine ethyl ester hydrochloride was as follows: ethyl L-alanine ethyl ester hydrochloride (8.1 g, 52.4 mmol) was dissolved in ethanol-methylamine solution (36 mL, 289 mmol), and the reaction was stirred for 97 hours. Upon completion of the reaction, the solvent was removed by evaporation. The residue was dissolved in 4 M potassium carbonate solution (30 mL) and saturated sodium bicarbonate solution (20 mL) and subsequently extracted with chloroform (5 × 25 mL). The organic phases were combined, dried over sodium carbonate and evaporated to give the crude (S)-2-amino-N-methylpropionamide as a red oil (3.62 g, 35.5 mmol, 68% yield). The free amine (1.9 g, 18.5 mmol) was dissolved in ether (200 mL) and treated by passing hydrogen chloride gas for 10 min. At the end of the reaction, the product was collected by filtration and washed with ether to afford (S)-2-amino-N-methylpropionamide hydrochloride as clarified crystals (2.2 g, 16.0 mmol, 86% yield). The product was further purified by recrystallization from ethanol and hexane; melting point 213-215 °C; [α]D25 +19.6 (c 0.1, CH3OH); νmax (NaCl disk)/cm-1 3408, 1674, 1514, 1417, 1275, 1169; δH (400 MHz, D2O) 3.85 (1H, q, J 7.1 Hz, CH), 2.60 (3H, s, NCH3), 1.32 (3H, d, J 7.1 Hz, CCH3); δC (100 MHz, D2O) 174.1 (C), 51.2 (CH), 28.5 (CH3), 19.2 (CH3).

References

[1] Tetrahedron, 2011, vol. 67, # 23, p. 4263 - 4267