918417-27-3Relevant articles and documents
Synthesis of various acylating agents directly from carboxylic acids
Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
supporting information, p. 1622 - 1632 (2020/04/27)
A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
Iron-Catalyzed Michael Addition of Ketones to Polar Olefins
Zhang, Di-Han,Knelles, Jakob,Plietker, Bernd
supporting information, p. 2469 - 2479 (2016/08/16)
The base metal complex tetrabutylammonium nitrosyltricarbonylferrate {Bu4N[Fe(CO)3(NO)] (TBA[Fe])} – catalyzes the conjugate addition of ketones to polar olefins. The reaction is applicable to a wide range of substrates leading to interesting building blocks for organic synthesis. Clear indications for an acid-base type rather than a C?H activation pathway exist. (Figure presented.).
PROCESS FOR MAKING CGRP RECEPTOR ANTAGONISTS
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Page/Page column 66, (2013/12/03)
The disclosure encompasses a novel process for making piperidinone carboxamide indane and azainane derivatives, having less steps and improved yields as compared to previous synthetic methods for making these compounds, which are CGRP receptor antagonists, useful for the treatment of migrane. Conditions for an amide bond formation between an acid and amine include for example reacting the compounds of Formulae B (after salt break) and C with an amide coupling reagent and optionally an additive and an acid and/or a base in a non-reactive solvent.
