61342-58-3Relevant academic research and scientific papers
Convenient primary amidation of N-protected phenylglycine and dipeptides without racemization or epimerization
Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki
, p. 394 - 396 (2014/01/06)
Primary amidation of N-protected phenylglycine and dipeptide proceeded easily to afford the corresponding amides in 57-95% yields with 99% ee and 81-99% de, respectively. The procedure is very easy to avoid racemization and epimerization of the products in the reactions by keeping exactly the reaction temperature at -15 C when the activation of carboxylic acids, followed by the reaction of the mixed carbonic carboxylic anhydride with NH4Cl.
Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives
Tomassetti, Mara,Fanì, Michela,Bianchini, Gianluca,Giuli, Sandra,Aramini, Andrea,Colagioia, Sandro,Nano, Giuseppe,Lillini, Samuele
supporting information, p. 6247 - 6250 (2013/10/22)
Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application.
An expedient route to the tetrazole analogues of α-amino acids
Demko, Zachary P.,Sharpless, K. Barry
, p. 2525 - 2527 (2007/10/03)
(Matrix presented) Convenient conditions are described for the transformation of α-aminonitriles to the tetrazole analogues of α-amino acids. Refluxing the starting material in water/2-propanol at 80 °C with sodium azide and catalytic zinc bromide affords
