L-Homoserine lactone hydrochloride

Chemical Properties

White Solid

Uses

(S)-α-Amino-γ-butyrolactone hydrochloride can be used:

• As a precursor for the preparation of amino-keto-alcohols and β-amino acids.
• To prepare N-acylhomoserine lactone (AHL) analogs by reacting with substituted 2-chloro-N-phenylacetamide and different halides.
• As a starting material for the synthesis of L-discadenine.

Synthesis

The general procedure for synthesizing L-homoserine lactone hydrochloride from L-homoserine is as follows: mix L-homoserine (0.84 mol) with 600 mL of concentrated hydrochloric acid (6.1 mol). The reaction mixture was stirred for about 15 minutes until all solids were completely dissolved. Subsequently, the water was removed by distillation under reduced pressure over a period of 1.5 hours. Finally, the residue was dried. The yield of this step was 99% to give 2-amino-4-butyrolactone hydrochloride.

References

[1] Patent: US7368600, 2008, B2. Location in patent: Page/Page column 16-17
[2] Tetrahedron Asymmetry, 1995, vol. 6, # 11, p. 2819 - 2828
[3] Patent: US2011/53890, 2011, A1. Location in patent: Page/Page column 3
[4] Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4516 - 4529
[5] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6500 - 6502