42801-75-2

Upstream product

• 41345-82-8 C₄H₆Cl₂O₂S 
• 80-63-7 methyl 2-chloroacrylate 
• 108-98-5 thiophenol 
• 292638-85-8 acrylic acid methyl ester 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 88347-74-4 α-Azido-β-(phenylthio)propansaeure-methylester 
• 81629-68-7 (E)-N-Acetyl-S-phenyl-α,β-didehydrocystein-methylester 
• 90237-84-6 (E)-N,N-Diacetyl-S-phenyl-α,β-didehydrocystein-methylester 
• 90237-79-9 (Z)-N-Acetyl-S-phenyl-α,β-didehydrocystein-methylester 
• 76604-94-9 2-Amino-3-(phenylthio)propansaeure-methylester 
• 88347-88-0 2-amino-3-phenylmercapto-propionic acid methyl ester.HCl 
• 88347-90-4 S-phenyl-D,L-cysteine hydrochloride 
• 5437-52-5 2-(S)-amino-3-phenylsulfanylpropionic acid 

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.

Amino Acids, 2. N-Acetyl α,β-Didehydro α-Amino Acid Esters from α-Azidocarboxylic Acid Esters and Acetic Anhydride by Nitrogen Elimination with Rhenium Catalysts

α-Azidocarboxylic acid esters 2 react with acetic anhydride in presence of catalytic amounts of rhenium heptasulfide and - if necessary - by addition of hydrochloric acid to give N-acetyl 3 or/and N,N-diacetyl-α,β-didehydro-α-amino acid esters 4 in very g