73246-45-4Relevant articles and documents
Optical methyl 2-chloropropionate synthesis by decomposition of methyl 2-(chlorocarbonyloxy)propionate with hexaalkylguanidinium chloride hydrochloride
Violleau, Frédéric,Thiébaud-Roux, Sophie,Borredon, Elisabeth,Le Gars, Pierre
, p. 8607 - 8612 (2002)
The decomposition of methyl S-(-)-2-(chlorocarbonyloxy)propionate in the presence of hexaalkylguanidinium chloride hydrochloride was confirmed to correspond to a nucleophilic substitution of the second order. However, racemization occured by the contact between the catalyst and methyl R-(+)-2-chloropropionate (I). This phenomenon is caused by the exchange between the chloride ion from catalyst and the chlorine atom of (I) according to a SN2 mechanism as well.
A synthetic S-2-chloropropionic acid methyl ester method
-
Paragraph 0036-0039, (2017/03/17)
The invention discloses a method for synthesizing S-2-methyl chloropropionate. The method comprises the following steps of: (1) preparing a Vilmerier reagent: adding a chlorinating agent into a reaction kettle, adding short chain aliphatic series dropwise to replace amide to serve as a solvent, and reacting under the stirring condition to obtain a Vilmerier reagent solution; (2) synthesizing S-2-methyl chloropropionate: adding a small amount of solvent into the Vilmerier reagent solution obtained in the step 1 to obtain a mixed solution, adding R-methyl lactate into the mixed solution dropwise, and stirring to perform chlorination to obtain a product solution, namely the S-2-methyl chloropropionate solution; and (3) washing the S-2-methyl chloropropionate solution obtained in the step 2, desolventizing and distilling to obtain the product S-2-methyl chloropropionate. The synthesis method is mild in reaction condition, easy to operate, low in environmental pollution and suitable for large-scale industrialized production.
Asymmetric reduction of 2-chloroacrylic acid to (S)-2-chloropropionic acid by a novel reductase from Burkholderia sp. WS
Kurata, Atsushi,Kurihara, Tatsuo,Kamachi, Harumi,Esaki, Nobuyoshi
, p. 2837 - 2839 (2007/10/03)
Burkholderia sp. WS has a novel enzyme that catalyzes the asymmetric reduction of 2-chloroacrylic acid to yield (S)-2-chloropropionic acid, which is used as a building block for the synthesis of aryloxyphenoxypropionic acid herbicides. NADPH is required as a co-substrate for this reaction.