74378-95-3

Upstream product

• 67-56-1 methanol 
• 5680-65-9 2-amino-3-(benzylthio)propionic acid 
• 26826-81-3 benzenemethanesulfenyl chloride 
• 100-53-8 phenylmethanethiol 
• 60741-22-2 2-Chlor-3-(benzylthio)propansaeure-methylester 
• 88347-75-5 2-Azido-3-(benzylthio)propansaeure-methylester 

Downstream Products

• 44641-43-2 cysteine methyl ester 
• 128070-21-3 5-benzylthiomethyl-4,5-dihydro-1,2,4-triazin-6(1H)-one 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING SULFUR-CONTAINING AMINO ACIDS

The present invention relates to a process for producing a sulfur-containing amino acid, comprising a step of oxidizing a 2-aminoethanol compound having, at position 2, a sulfur-containing hydrocarbon group having 1 to 24 carbon atoms in the presence of copper and water.

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.

S-substituted 2-azido-3-mercapto-propionic acid ester and process for its production and use

The subject matter of the invention are S-substituted 2-azido-3-mercapto-propionic acid esters of the general formula STR1 in which R1 is a methyl or ethyl group and R2 is an unsubstituted or substituted alkyl group, a cycloalkyl group, an unsubstituted or substituted aromatic or heteroaromatic group or a benzyl group, and a process for their production by reaction of a methyl or ethyl ester of 2-chloroacrylic acid with a corresponding thiol to form an S-substituted 2-chloro-3-mercapto-propionic acid ester and subsequently exchanging the chlorine atom with an azido group as well as use of the compounds of formula (I) as intermediate products in the production of D,L-cysteine or derivatives of D,L-cysteine.