80213-06-5

Upstream product

• 5053-63-4 3-amino-1-phenylpropan-1-ol 
• 1256544-03-2 ethyl 2-(benzamidomethyl)-3-oxo-3-phenylpropanoate 
• 6282-02-6 N-(hydroxymethyl)benzamide 
• 31537-54-9 N-(3-oxo-3-phenylpropyl)benzamide 
• 38792-42-6 N-(chloromethyl)benzamide 
• 98-88-4 benzoyl chloride 
• 26385-07-9 N-(2-chloro-ethyl)-benzamide 
• 100-52-7 benzaldehyde 
• 150932-87-9 N-lithio-N-(2-lithioethyl)benzamide 

Relevant academic research and scientific papers

One drop chemical derivatization - DESI-MS analysis for metabolite structure identification

Structural elucidation of metabolites is an important part during the discovery and development process of new pharmaceutical drugs. Liquid Chromatography (LC) in combination with Mass Spectrometry (MS) is usually the technique of choice for structural identification but cannot always provide precise structural identification of the studied metabolite (e.g. site of hydroxylation and site of glucuronidation). In order to identify those metabolites, different approaches are used combined with MS data including nuclear magnetic resonance, hydrogen/deuterium exchange and chemical derivatization followed by LC-MS. Those techniques are often time-consuming and/or require extra sample pre-treatment. In this paper, a fast and easy to set up tool using desorption electrospray ionization-MS for metabolite identification is presented. In the developed method, analytes in solution are simply dried on a glass plate with printed Teflon spots and then a single drop of derivatization mixture is added. Once the spot is dried, the derivatized compound is analyzed. Six classic chemical derivatizations were adjusted to work as a one drop reaction and applied on a list of compounds with relevant functional groups. Subsequently, two successive reactions on a single spot of amoxicillin were tested and the methodology described was successfully applied on an in vitro incubated alprazolam metabolite. All reactions and analyses were performed within an hour and gave useful structural information by derivatizing functional groups, making the method a time-saving and efficient tool for metabolite identification if used in addition or in some cases as an alternative to common methods.

3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation

The catalytic asymmetric reduction of ethyl-2-(benzamidomethyl)-3-oxo- phenylpropanoate was realized with high enantiomeric and diastereoisomeric excesses via biotransformation using whole cells of different yeasts and asymmetric hydrogenation with Ru(II)

N-LITHIO-N-(2-LITHIOETHYL)- AND N-LITHIO-N-(3-LITHIOPROPYL)-BENZAMIDE: DIRECT PREPARATION AND SYNTHETIC APPLICATIONS OF 2-LITHIOETHYL- AND 3-LITHIOPROPYL-AMINE EQUIVALENTS

The successive reaction of 2-chloroethyl and 3-chloropropyl-benzamide with n-butyl-lithium and lithium naphthalenide at temperatures ranging between -78 and -50 deg C leads to N-lithio-N-(2-lithioethyl)- and N-lithio-N-(3-lithiopropyl)benzamide , which by treatment with different electrophiles (H2O, D2O, Me2S2, CO2, PriCHO, PhCHO, Me2CO, Ph2CO, and O2) yields the expected functionalized benzamides .The acidic and basic hydrolysis of compounds (10) and (11) gives different results depending on the structure of the substrate and the reaction conditions.

N-LITHIO-N-(2-LITHIOETHYL)BENZAMIDE: DIRECT PREPARATION OF A 2-LITHIOETHYLAMINE EQUIVALENT

The successive reaction of 2-chloroethylbenzamide with n-butyl-lithium and lithium naphthalenide at -78 deg C leads to N-lithio-N-(2-lithioethyl)benzamide, which reacts with different electrophiles (H2O, D2O, Me2S2, CO2, i-PrCHO, PhCHO, Me2CO, Ph2CO) to afford the expected 2-functionalized benzamides.