88347-75-5

Upstream product

• 60741-22-2 2-Chlor-3-(benzylthio)propansaeure-methylester 
• 26826-81-3 benzenemethanesulfenyl chloride 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 5680-65-9 2-amino-3-(benzylthio)propionic acid 
• 74378-95-3 2-Amino-3-(benzylthio)propansaeure-methylester 
• 5462-08-8 S-Benzyl-L-cysteine methyl ester hydrochloride 
• 6304-78-5 3-benzylsulfanyl-2R-aminopropionic acid hydrochloride 

Relevant academic research and scientific papers

Amino Acids, 12. - Syntheses of DL-Cysteines from Acrylic Acid Derivatives

The addition of sulfenyl chlorides 1 to 2-alkenoic acid esters 2 gives mixtures of 2(3)-chloro-3(2)-thioalkenoic acid esters 3/4, whereas the addition of thiols 7 to methyl 2-chloro-2-propenoate (6) results in the formation of methyl 2-chloro-3-thiopropanoates 3 only.The dependence of the isomerization of 3 to 4 on the reaction conditions was investigated; at higher temperatures the formation of 4 is especially favored.At temperatures below 55 deg C the 2-azido compounds 8 are obtained without isomerization from 3 by reaction with sodium azide in the presence of a PT catalyst.Cysteine derivatives 9 or 10, resp., are obtained by hydrogenation of 8 with H2S/pyridine/H2O or with H2/Re2S; the overall yields of 9 or 10, resp., starting from 6 are as high as 70percent.DL-Cysteine is obtained in good overall yields as hydrochloride hydrate 16 by HCl-catalyzed hydrolysis of the 2-thiazolines 15a*HCl and 15e, which are prepared by HCl-catalyzed addition of thioacetamide (11a) to α-chloroacrylic acid (12) or the amide 13 and consecutive ring closure.