155905-76-3Relevant articles and documents
Polybasic nitrogen heterocyclic non-natural chiral amino acid and synthesis method thereof
-
Paragraph 0093; 0110; 0112; 0113, (2018/11/22)
The invention relates to a polybasic nitrogen heterocyclic non-natural chiral amino acid and a synthesis method thereof. The amino acid can be applied to molecule building for antibiotic synthesis. According to the synthesis method, 2-aminodiethyl malonate and halogenated alkanes carry out substitution reactions, cyclization reactions, and decarboxylation reactions, and the reaction products are split to obtain the polybasic nitrogen heterocyclic non-natural chiral amino acid. The provided novel synthesis method has the advantages of simple synthesis route, low cost, convenient operation, andeasiness for commercial production, the chiral purity of obtained products is high, and the application prospect is good.
NITROGEN CONTAINING BICYCLIC COMPOUNDS AND THEIR USE IN TREATMENT OF BACTERIAL INFECTIONS
-
Page/Page column 25, (2017/01/23)
Compounds of Formula (I), their preparation, and use in preventing or treating a bacterial infection are disclosed.
Asymmetrie substitutions of 2-lithiated N-boc-piperidine and N-boc-azepine by dynamic resolution
Coldham, Iain,Raimbault, Sophie,Whittaker, David T. E.,Chovatia, Praful T.,Leonori, Daniele,Patel, Jignesh J.,Sheikh, Nadeem S.
experimental part, p. 4082 - 4090 (2010/07/10)
Proton abstraction of N-tertbutoxycarbonyl-piperidine (N-Boc-piperidine) with sBuLi and TMEDA provides a racemic organolithium that can be resolved using a chiral ligand. The enantiomeric organolithiums can interconvert so that a dynamic resolution occurs. Two mechanisms for promoting enantioselectivity in the products are possible. Slow addition of an electrophile such as trimethylsilyl chloride allows dynamic resolution under kinetic control (DKR). This process occurs with high enantioselectivity and is successful by catalysis with substoichiometric chiral ligand (catalytic dynamic kinetic resolution). Alternatively, the two enantiomers of this organolithium can be resolved under thermodynamic control with good enantioselectivity (dynamic thermodynamic resolution, DTR). The best ligands found are based on chiral diamino-alkoxides. Using DTR, a variety of electrophiles can be used to provide an asymmetric synthesis of enantiomerically enriched 2-substituted piperidines, including (after Boc deprotection) the alkaloid (+)-ss-conhydrine. The chemistry was extended, albeit with lower yields, to the corresponding 2-substituted sevenmembered azepine ring derivatives.