75893-06-0Relevant academic research and scientific papers
Method of producing an amide
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Page/Page column 2; 7, (2008/06/13)
The present invention discloses a new method for synthesizing an amide based on a fundamental mechanistic revision of the reaction of thio acids and organic azides. Moreover, the application of this method to the selective preparation of several classes of complex amides in nonpolar and polar solvents, including water, is provided.
The reaction of thio acids with azides: A new mechanism and new synthetic applications
Shangguan, Ning,Katukojvala, Sreenivas,Greenberg, Rachel,Williams, Lawrence J.
, p. 7754 - 7755 (2007/10/03)
A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water. Copyright
REACTION OF SULFOXIDES WITH NITRILES IN PRESENCE OF TRIFLUOROACETIC ANHYDRIDE AND TRIFLUOROACETIC ACID: A CASE OF RITTER REACTION OF PUMMERER INTERMEDIATE
Vankar, Yashwant D.,Rao, C. Trinadha
, p. 3405 - 3410 (2007/10/02)
Reaction of various sulfoxides 9, with nitriles 10 in presence of trifluoroacetic anhydride and trifluoroacetic acid gave the corresponding amides 11 via a Ritter reaction on Pummerer intermediate derived from the sulfoxides.
STUDIES ON PEPTIDES. XCVI. BEHAVIOR OF S-ACETAMIDOMETHYLCYSTEINE SULFOXIDE UNDER DEPROTECTING CONDITIONS IN PEPTIDE SYNTHESIS
Yajima, Haruaki,Akaji, Kenichi,Funakoshi, Susumu,Fujii, Nobutaka,Irie, Hiroshi
, p. 1942 - 1945 (2007/10/02)
The sulfoxide of Boc-Cys(S-acetamidomethyl)-OH was prepared by oxidation with sodium perborate.Mercuric acetate and iodine failed to cleave the S-protecting group from sulfoxide.Hydrogen fluoride and methanesulfonic acid partially converted the sulfoxide to S-p-methoxyphenylcysteine in the presence of anisole.A reducing reagent, thiophenol, converted the sulfoxide to acetamidomethyl phenyl sulfide and Nα-Boc-S-(phenylthio)cysteine.Keywords - S-acetamidomethylcysteine sulfoxide; mercuric acetate treatment; iodine treatment; hydrogen fluoride treatment; methanesulfonic acid treatment; thiophenol treatment
