Ethyl L-alaninate hydrochloride synthesis
- Product Name:Ethyl L-alaninate hydrochloride
- CAS Number:1115-59-9
- Molecular formula:C5H12ClNO2
- Molecular Weight:153.61
64-17-5
56-41-7
1115-59-9
L-alanine (3.56 g, 0.04 mol) was dissolved in ethanol (30 mL) at -5 °C and thionyl chloride (3.6 mL) was added slowly and dropwise, keeping stirring. Subsequently, the reaction mixture was warmed up to 78 °C and the reaction was refluxed in ethanol for 1.5 hours. Upon completion of the reaction, the solvent was removed by vacuum distillation to afford L-alanine ethyl ester hydrochloride (2a) in over 80% yield. The physical constants of the product 2a were in agreement with the data reported in literature [24].
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Yield:1115-59-9 98%
Reaction Conditions:
in ethanol
Steps:
1.a a)
a) L-Alanine ethyl ester hydrochloride (2) Hydrogen chloride gas was bubbled into a suspension of L-alanine (1) (100 g, 1.12 mol) in dry ethanol (800 ml) and the solution was refluxed for 2 hours. After concentration in vacuo the compound was recrystallized from ethanol-diethyl ether giving the title ester (2) (168.2g, 98%) as a white solid. δH (200 MHz; D2 O) 1.11 (3H, t, J=7.1, CH2 CH3), 1.37 (3H, d, J=7.4, CHCH3), 4.03 (1H, q, J=7.2, CHCH3), 4.09 (2H, q, J=7.2, CH2 CH3), 4.16 (2H, s, NH2); δC (125 MHz; D2 O) 13.98 (CH3), 15.90 (CH3), 49.65 (CH), 64.29 (CH2), 171.57 (CO).
References:
Oxford Asymmetry International plc US5801249, 1998, A
![L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester](/CAS/20200515/GIF/51814-53-0.gif)
51814-53-0
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1115-59-9
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