DL-THREONINE METHYL ESTER HYDROCHLORIDE Chemical Properties

Melting point:

125℃

storage temp. 

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

form 

solid

color 

Beige

Safety Information

WGK Germany 

3

HS Code 

2922500090

MSDS

• Language:English Provider:SigmaAldrich

DL-THREONINE METHYL ESTER HYDROCHLORIDE Usage And Synthesis

Uses

Dl-threonine methyl ester HCl

Synthesis

The general procedure for the synthesis of L-threonine methyl ester hydrochloride from methanol and (2S,3S)-2-amino-3-hydroxybutanoic acid was as follows: a mixture of (2S,3S)-2-amino-3-hydroxybutanoic acid (5.4 g, 24.6 mmol) and 6N HCl (60 mL) was refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was extracted with ether (3 x 70 mL) to remove the benzoic acid. The aqueous phase was concentrated to dryness under reduced pressure and the residue was further dried under high vacuum overnight to give crude allo-L-threonine. Methanol (25 mL) was cooled to 0 °C and thionyl chloride (1.80 mL, 25.2 mmol) was added slowly and dropwise. Crude allo-L-threonine was added to the resulting HCl methanol solution and the reaction mixture was heated to reflux for 1 hour. After completion of the reaction, the solvent was removed under vacuum and another batch of HCl methanol solution prepared in the same manner was added and again heated to reflux for 1 hour. Finally, the solvent was removed in vacuum to give allo-L-threonine methyl ester hydrochloride (4.15 g, 98% overall yield in two steps) as a red solid. The product was confirmed by 1H NMR (300 MHz, CD3OD): δ1.27 (d, J=6.6 Hz, 3H), 4.03 (d, J=3.3 Hz, 1H), 4.27-4.33 (m, 1H); 13C NMR (75 MHz, CD3OD): δ17.13,58.17,65.11,167.62; MS ( ESI, positive): m/z 134 [M+H]+.

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547
[2] Helvetica Chimica Acta, 1957, vol. 40, p. 1531,1544
[3] Journal of Organic Chemistry, 1997, vol. 62, # 21, p. 7364 - 7375
[4] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10046 - 10057
[5] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 6017 - 6021

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