53821-16-2Relevant academic research and scientific papers
Reaction of organozinc halides with aryl isocyanates
Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
supporting information, p. 2588 - 2593 (2013/03/28)
Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
A facile protocol for N-Cbz protection of amines in PEG-600
Zhang, Chun Lin,Zhang, Dong Feng,Zhao, Hong Yi,Lin, Zi Yun,Huang, Hai Hong
experimental part, p. 789 - 792 (2012/08/08)
An efficient and eco-friendly protocol for the chemoselective N-benzyloxycarbonylation of amines was described. The reaction of amines with benzyl chloroformate (Cbz-Cl) in the presence of PEG-600 at room temperature afforded the corresponding N-Cbz derivatives in excellent yields. The method is applicable to the N-Cbz protection of aliphatic (acyclic and cyclic) and aromatic amines.
Structure-based design, synthesis, and structure-activity relationship studies of HIV-1 protease inhibitors incorporating phenyloxazolidinones
Ali, Akbar,Reddy, G. S. Kiran Kumar,Nalam, Madhavi N. L.,Anjum, Saima Ghafoor,Cao, Hong,Schiffer, Celia A.,Rana, Tariq M.
scheme or table, p. 7699 - 7708 (2010/12/30)
A series of new HIV-1 protease inhibitors with the hydroxyethylamine core and different phenyloxazolidinone P2 ligands were designed and synthesized. Variation of phenyl substitutions at the P2 and P2' moieties significantly affected the binding affinity and antiviral potency of the inhibitors. In general, compounds with 2- and 4-substituted phenyloxazolidinones at P2 exhibited lower binding affinities than 3-substituted analogues. Crystal structure analyses of ligand-enzyme complexes revealed different binding modes for 2- and 3-substituted P2 moieties in the protease S2 binding pocket, which may explain their different binding affinities. Several compounds with 3-substituted P2 moieties demonstrated picomolar binding affinity and low nanomolar antiviral potency against patient-derived viruses from HIV-1 clades A, B, and C, and most retained potency against drug-resistant viruses. Further optimization of these compounds using structure-based design may lead to the development of novel protease inhibitors with improved activity against drug-resistant strains of HIV-1.
Synthesis of N-Benzylated Anilines from the Reaction of Anilines and Benzyl Chloroformate
Pati, Hari,Weisbruch, Paul,Lemon, Adrienne,Lee, Moses
, p. 933 - 940 (2007/10/03)
Reactions of benzyl chloroformate with a series of substituted anilines produced N-carbobenzyloxy "CBZ" products along with the unexpected N-benzylated "Bn" compounds. Reaction of aniline, 1a, gave the CBZ, or 2a, and Bn, or 3a, products in 29% and 14% yi
Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI
Salvatore, Ralph N,Chu, Feixia,Nagle, Advait S,Kapxhiu, Elona A,Cross, Richard M,Jung, Kyung Woon
, p. 3329 - 3347 (2007/10/03)
Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAI via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcohols and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcohols and amines were examined, using a wide array of alkyl halides, and the results demonstrated this methodology was highly chemoselective. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the corresponding products exclusively, offering a wide variety of applications such as novel protecting groups and peptidomimetic syntheses.
Boron trifluoride promoted cleavage of benzyl carbamates
Subhas Bose,Thurston, David E.
, p. 6903 - 6906 (2007/10/02)
A new efficient method for the cleavage of benzyl carbamates (CBZ protective groups) is described that involves a hard acid (BF3·OEt2) - soft nucleophile (EtSH) system. Unlike other available methods, this combination avoids the reduction of olefins, acetylenes, imines, halides and nitro groups, or the possibility of carboxylic ester hydrolysis.
