107902-67-0

Basic information

• Product Name: 4-Thiazolidinone,5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-
• Synonyms: LY 213829;Tazofelone
• CAS NO: 107902-67-0
• Molecular Formula: C18H27 N O2 S
• Molecular Weight: 321.484
• Mol File: 107902-67-0.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinone,5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinone,5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-(107902-67-0)
• EPA Substance Registry System: 4-Thiazolidinone,5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-(107902-67-0)

Safety Data

• Hazardous Substances Data: 107902-67-0(Hazardous Substances Data)

Upstream product

• 137506-94-6 (Z)-5-(3,5-di-tert-butyl-4-hydroxyphenylmethylene)-4-oxo-2-thiazolidinethione 
• 107902-68-1 5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methyl}-2-thioxo-4-thiazolidinone 
• 188532-24-3 3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-hydroxymethylsulfanyl-propionamide 
• 50-00-0 formaldehyd 
• 188532-21-0 3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-mercapto-propionamide 
• 67739-23-5 5-(4-hydroxy-3,5-di-tert-butylbenzylidene)rhodanine 
• 188532-26-5 5-(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4-thiazolidinedione 

Downstream Products

• 107902-67-0 (+)-5-<<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>methyl>-4-thiazolidinone 
• 107902-67-0 (-)-5-<<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>methyl>-4-thiazolidinone 
• 136433-34-6 Tazofelone sulfoxide 

Relevant articles and documents

Substrate specificity of the kinetic resolution of sulfides by enantioselective sulfoxide formation

The kinetic resolution of tazofelone (1) has been reported. The resolution of this sulfide was accomplished via enantioselective sulfoxide formation with tert-Bu hydroperoxide in the presence of a chiral tartrate/titanium complex. The resolution was performed on analogues of compound 1 in order to explore the substrate specificity of the kinetic resolution, These experiments have shown that the success of the enantioselective oxidation of this sulfide by tert-Bu hydroperoxide is greatly influenced by the nature of the neighboring amide functionality.

A novel protecting group for hindered phenols

Boc2O and DMAP were used to protect hindered phenols as their Boc derivatives under mild conditions. Deprotection conditions were developed to suppress loss of a tert-butyl group from the aromatic ring, or alkylation of an additional tert-butyl group at an unsubstituted ortho or para position.

Alternate crystal form of Tazofelone

PCT No. PCT/US96/14132 Sec. 371 Date Feb. 25, 1998 Sec. 102(e) Date Feb. 25, 1998 PCT Filed Sep. 3, 1996 PCT Pub. No. WO97/09320 PCT Pub. Date Mar. 13, 1997The instant invention provides novel crystalline Form II of (+/-)-5-{[3,5-bis(1,1dimethylethyl)-4-hydroxyphenyl]methyl}-4-thiazolidinone having an x-ray powder diffraction patter with specific d spacings useful for treating inflammation, inflammatory bowel disease, allergies, arthritis and hypoglycemia utilizing the novel physical form as well as pharmaceutical compositions containing the same. A process for preparing Form II Tazofelone is described.

Product structure as a function of reaction conditions in the reaction of formaldehyde with an alpha-mercapto amide

Treatment of mercapto amide (3) with formaldehyde and acid or base results in products whose structures are a function of the reaction conditions. Lactone (8), hemithioacetal (9), and dimer (7) were formed in good yields under acidic reaction conditions.