L-Alanine benzyl ester hydrochloride Chemical Properties

Melting point:

140-142°C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO, Methanol, Water

form 

Powder

color 

White to off-white

optical activity

Consistent with structure

CAS DataBase Reference

5557-83-5(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

L-Alanine benzyl ester hydrochloride Usage And Synthesis

Chemical Properties

L-Alanine benzyl ester hydrochloride is White Solid

Uses

L-Alanine benzyl ester hydrochloride is a benzoxazine derivative used as an additive in the microemulsion formulation for topical applications of acyclovir. A reagent in the preparation of collagenase inhibitors.

Uses

L-Alanine benzyl ester (ALAB) may be used as an organic reagent and as a cationic charge inducer in microemulsions.

Synthesis

The general procedure for the synthesis of benzyl 2-aminopropionate hydrochloride from L-alanine and benzyl alcohol is as follows: Example 43: Preparation of HCl-Ala-OBzl 1. 1070 mg (0.012 mol) of L-alanine was added to a mixed solution of 25 mL of benzyl alcohol and 5 g of polyphosphoric acid. 2. The reaction mixture was stirred at 90-95 °C for 4 h. The progress of the reaction was monitored by TLC (unfolding agent: chloroform/methanol, 20:1) until the L-alanine disappeared completely. 3. The reaction mixture was poured into 200 mL of aqueous solution containing 10 mL of concentrated hydrochloric acid and stirred thoroughly. 4. The reaction mixture was extracted with ether (50 mL x 3) to separate the organic and aqueous phases. 5. The organic phase was washed with 2% hydrochloric acid (30 mL x 3). 6. The aqueous phase was combined and the pH was adjusted to 10 with sodium carbonate. 7. The aqueous phase was extracted with 100 mL of ether and the organic phase was dried with anhydrous Na2SO4. 8. The dried organic phase was filtered and hydrogen chloride gas was passed into the filtrate until (S)-benzyl (S)-2-aminopropionate hydrochloride precipitated completely. 9. The precipitate was collected by filtration and dried over anhydrous CaCl2 to give 1500 mg (58% yield) of (S)-benzyl 2-aminopropionate hydrochloride crystals. 10. The melting point of the product was determined to be 140-142°C.

References

[1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1197 - 1201
[2] Patent: US2005/80015, 2005, A1. Location in patent: Page/Page column 10-11
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6220 - 6229

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