511544-19-7Relevant academic research and scientific papers
Scale-up Synthesis of (R)- and (S)-N-(2-Benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide Hydrochloride, A Versatile Reagent for the Preparation of Tailor-Made α- And β-Amino Acids in an Enantiomerically Pure Form
Romoff, Todd T.,Palmer, Andrew B.,Mansour, Noel,Creighton, Christopher J.,Miwa, Toshio,Ejima, Yuki,Moriwaki, Hiroki,Soloshonok, Vadim A.
, p. 732 - 739 (2017)
Unusual amino acids are of crucial importance to the synthesis of bioactive peptides and new chemical entities. Innovative methodology is always needed for the preparation of enantiomerically pure amino acids that does not rely on tedious resolution procedures. The proline-derived ligands (R)- and (S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide are outstanding, versatile, and recyclable reagents for the synthesis of tailor-made α- and β-amino acids. Here we report initial studies of the scale-up synthesis of the HCl salt of these reagents on the 100 g scale. The results demonstrate an increased efficiency and environmental friendliness of the bench-scale procedure and provides a firm foundation for the manufacture on multikilogram and larger scales.
SYNTHESIS OF A-AMANITIN AND ITS DERIVATIVES
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Page/Page column 30, (2021/01/29)
The present invention relates to the chemical synthesis of α-amanitin and its derivatives. The present invention also relates to intermediate products of the α-amanitin synthesis.
Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands
Zhou, Shengbin,Wang, Jiang,Chen, Xia,Acena, Jose Luis,Soloshonok, Vadim A.,Liu, Hong
supporting information, p. 7883 - 7886 (2014/08/05)
The first chemical method for resolution of N,C-unprotected β-amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β-substituted-β-amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β-aryl, β-heteroaryl, and β-alkyl-derived β-amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti-diabetic drug sitagliptin. The nick of time: A chemical method for resolution of unprotected β-amino acids rac-1 was developed through enantioselective formation and disassembly of nickel(II) complexes to deliver the target β-substituted β-amino acids in good yields and excellent enantioselectivity. The chiral ligands are inexpensive and can be quantitatively recycled. The procedure was used for the preparation of anti-diabetic drug sitagliptin.
Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-α-amino acids
Belokon,Maleev,Petrosyan,Savel'eva,Ikonnikov,Peregudov,Khrustalev,Saghiyan
, p. 1593 - 1599 (2007/10/03)
The synthesis of new chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(3,4-dichlorobenzyl)-pyrrolidine-2-carboxamide (1a), (S)-N-(2-benzoylphenyl)-1-(pentafluorobenzyl)pyrrolidine-2-carboxamide (1b), and (S)-N-(2-benzoylphenyl)-1-(4-isopropoxytetrafluorobenzyl) pyrrolidine-2-carboxamide (1c) and their application in the asymmetric synthesis of amino acids using NiII complexes of their Schiff's bases with alanine and glycine are described. Compound la is particularly appropriate for highly stereoselective synthesis of α-methyl-α -amino acids with high enatiomeric purity (ee >95%).
