L-Alanine isopropyl ester hydrochloride Chemical Properties

Melting point:

85 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

color 

White to Orange to Green

optical activity

Consistent with structure

Stability:

Very Hygroscopic

InChI

InChI=1/C6H13NO2.ClH/c1-4(2)9-6(8)5(3)7;/h4-5H,7H2,1-3H3;1H/t5-;/s3

InChIKey

YAQKNCSWDMGPOY-JEDNCBNOSA-N

SMILES

C(=O)([C@@H](N)C)OC(C)C.Cl |&1:2,r|

Safety Information

HS Code 

2922498590

L-Alanine isopropyl ester hydrochloride Usage And Synthesis

Uses

L-Alanine isopropyl ester hydrochloride is a reagent used in the synthesis of anti- hepatitis C virus prodrugs based on imidazotriazine and pyrrolotriazine molecules. Further, it reacts with (1R:2R)-2-Hydroxy-πnanone-3 to prepare isopropyl (1R,2R,5R)-2′-[(2-hydroxypinan-3-ylene)amino]propanoate.

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

To a reaction flask equipped with a mechanical stirrer, reflux condenser tube, thermometer and under nitrogen protection was added L-alanine (5.0 g, 56.1 mmol) and 11.1% w/w isopropanol HCl solution (73.8 g, 224.5 mmol). The reaction mixture was heated to reflux temperature (80-85 °C) and kept for 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using a 7:3 ethanol-water mixture as eluent and ninhydrin as color developer. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove isopropanol and isopropyl acetate, and the residual solvent was removed by multiple azeotropic distillations to give the final product (R)-isopropyl (R)-2-aminopropionate hydrochloride in oil form (9.4 g, quantitative yield).

References

[1] Patent: WO2016/151542, 2016, A1. Location in patent: Page/Page column 19
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 20, p. 2622 - 2628
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1197 - 1201
[4] Patent: WO2015/38596, 2015, A1. Location in patent: Page/Page column 237; 238
[5] Patent: WO2016/145142, 2016, A1. Location in patent: Page/Page column 287

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