85303-65-7Relevant academic research and scientific papers
Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o -NosylOXY): A recyclable coupling reagent for racemization-free synthesis of peptide, amide, hydroxamate, and ester
Dev, Dharm,Palakurthy, Nani Babu,Thalluri, Kishore,Chandra, Jyoti,Mandal, Bhubaneswar
, p. 5420 - 5431 (2014/07/08)
Ubiquitousness of amide and ester functionality makes coupling reactions extremely important. Although numerous coupling reagents are available, methods of preparation of the common and efficient reagents are cumbersome. Those reagents generate a substantial amount of chemical waste and lack recyclability. Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY), the first member of a new generation of coupling reagents, produces byproducts that can be easily recovered and reused for the synthesis of the same reagent, making the method more environmentally friendly and cost-effective. The synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. The synthesis of the difficult sequences, for example, the islet amyloid polypeptide (22-27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH 2) and acyl carrier protein (65-74) fragment (H-Val-Gln-Ala-Ala-Ile- Asp-Tyr-Ile-Asn-Gly-OH), following the solid-phase peptide synthesis (SPPS) protocol and Amyloid β (39-42) peptide (Boc-Val-Val-IIe-Ala-OMe), following solution-phase strategy is demonstrated. Remarkable improvement is noticed with respect to reaction time, yield, and retention of stereochemistry. A mechanistic investigation and recyclability are also described.
Esterification of salicylic acid using Br?nsted acidic ionic liquid based on Keggin heteropoly acid
Bamoharram, Fatemeh F.,Heravi, Majid M.,Ebrahimi, Javad,Tavakoli-Hoseini, Nilofar
, p. 36 - 42 (2016/09/23)
For the first time, a newwater stable Br?nsted acidic ionic liquid based on Keggin heteroployacid (HPA) was used as environmentally benign catalytic medium in the esterfication of salicylic acid with aliphatic alcohols, CnH2n+1OH (n = 1-5) and benzylic alcohols, RC6H4CH2OH (R = H, NO2, OCH3). This ionic liquid (IL) afforded excellent yield in both thermal conditions and microwave irradiation. Maximum yields were observed under microwave irradiation. Different reaction runs were conducted by varying the reaction parameters such as molar ratio of reactants, weight of the IL, and reaction period in order to optimize the reaction. The IL was easily recovered and reused many times. No significant loss in catalytic activity was observed on recycling.
