117389-93-2

Upstream product

• 67-56-1 methanol 
• 75-15-0 carbon disulfide 
• 209741-93-5 (R)-2-(4-Methoxy-benzylamino)-3-[(R)-2-(4-methoxy-benzylamino)-2-methoxycarbonyl-ethyldisulfanyl]-propionic acid methyl ester 
• 209741-90-2 (R)-3-[(R)-2-Carboxy-2-(4-methoxy-benzylamino)-ethyldisulfanyl]-2-(4-methoxy-benzylamino)-propionic acid 
• 65776-11-6 (R)-3-mercapto-2-(4-methoxy-benzylamino)-propionic acid 
• 117389-69-2 2-(4-methoxybenzylthio)-4-methoxycarbonyl-Δ²-1,3-thiazoline 

Relevant academic research and scientific papers

Novel methods for the synthesis of 3-arylmethyl-4-thiazolidine carboxylic acid-2-thiones and their methyl esters

Reductive amination, using benzaldehyde derivatives and sodium borohydride, on L-cystine yields N,N'-di (arylmethyl) cystines 7a-c which can be converted into N, N'-di(arylmethyl) cystine dimethyl esters 8a-c by esterification. The reductive reaction by zinc, hydrochloric acid and methanol on the derivatives 7 and 8 yields the thiols 4a-c and 5a-c, respectively which on reaction with CS2 or EtOCS2K are further converted into 3-arylmethyl-4-thiazolidine carboxylic acid-2-thiones 1a-c and their methyl esters 2a-c. Compounds 2a-c are also produced by esterification of 1a-c. Fewer reaction steps and higher yields are the advantages of these methods.

Syntheses of (rac)3-Substituted 4-Methoxycarbonyl-1,3-thiazolidine-2-thiones via Rearrangement of a Substituted Group from exo-S to N in (rac)2-Substituted Thio-4-methoxycarbonyl-Δ2-1,3-thiazolines

Based on the previously obtained structural information, (rac)3-substituted 4-carboxy-1,3-thiazolidine-2-thiones 10 were designed as new aldose reductase inhibitors which might be helpful in treating the chronic complications of diabetes.After several trials to find efficient reaction conditions for preparation of the precursors 15 of compounds 10, a catalytic thermal rearrangement reaction of 14 proved to be practically available.Thus, various 3-substituted 4-methoxycarbonyl-1,3-thiazolidine-2-thiones 15a and 15d-t were readily synthesized by heating tha corresponding 2-substituted thio-Δ2-1,3-thiazolines 14a and 14d-t at 120 deg C in the presence of 0.1 mol eq of the corresponding halides 13a and 13d-t without any organic solvent (Sykes conditions).A plausible reaction pathway for the catalytic thermal rearrangement reaction of 14a or 14d-t is presented.Keywords - aldose reductase inhibitor; (rac)2-substituted thio-4-methoxycarbonyl-Δ2-1,3-thiazoline; (rac)3-substituted 4-methoxycarbonyl-1,3-thiazolidine-2-thione; Sykes-type reaction; rearrangement; stepwise cationic reaction; concerted bimolecular transition state

Substituent Effect of the Benzene Ring on Thermal Rearrangement of the Substituted Benzyl Group from exo-S to N(3) in (rac)2-Substituted Benzylthio-4-methoxycarbonyl-Δ2-1,3-thiazolines

The substituent effect of the benzene ring in the catalytic thermal rearrangement of the substituted benzyl group from exo-S to N(3) in compounds 1a-o was investigated.The reactivity order of the rearrangement with various substituents was as follows: (hi