Inagaki, Masanao published the artcileHighly E-Selective and Effective Synthesis of Antiarthritic Drug Candidate S-2474 Using Quinone Methide Derivatives, Application In Synthesis of 73343-04-1, the main research area is ditertbutylhydroxybenzylideneethylisothiazolidine dioxide preparation; isothiazolidine ditertbutylhydroxybenzylideneethyl dioxide preparation.
We have developed an efficient and E-selective synthesis of an antiarthritic drug candidate (E)-(5)-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-ethyl-1,2-isothiazolidine-1,1-dioxide (S-2474), in which α-methoxy-p-quinone methide is used as a key intermediate. α-Methoxy-p-quinone methide was revealed to be an equivalent to a p-hydroxy protected benzaldehyde. It reacts smoothly with α-sulfonyl carbanion to give 1,6-addition intermediates, which can be further processed to provide S-2474 directly in the presence of a base. This procedure gives S-2474 as an almost single isomer on the benzylidene double bond in excellent yield and thus is a very practical method adaptable to large-scale synthesis. The detailed mechanistic aspects are studied and discussed.
Journal of Organic Chemistry published new progress about ditertbutylhydroxybenzylideneethylisothiazolidine dioxide preparation; isothiazolidine ditertbutylhydroxybenzylideneethyl dioxide preparation. 73343-04-1 belongs to class isothiazole, name is 2-Ethylisothiazolidine 1,1-dioxide, and the molecular formula is C5H11NO2S, Application In Synthesis of 73343-04-1.
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com