227016-77-5

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 102-92-1 Cinnamoyl chloride 
• 850425-51-3 dimethoxyphosphoryl-N-[(S)-α-methylbenzyl]acetamide 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 193967-71-4 bromo<(S)-(1-phenylethyl)carbamoyl>methane 

Downstream Products

• 5668-19-9 (2S)-2-Benzylhexanoic acid 

Relevant academic research and scientific papers

METHOD FOR SYNTHESISING AMIDES

The present invention relates to a method for synthesising amides that is of general applicability. The method may be performed in vitro or in vivo. Cell lines for use in the in vivo methods also form aspects of the invention. The method for synthesising a non-natural amide comprises: a. reaction of a carboxylic acid with a naturally occurring CoA ligase or a variant thereof; and b. reaction of the product of step a with an amine in the presence of a naturally occurring acyltransferase or a variant thereof; with the proviso that where the CoA ligase and acyltransferase are both naturally occurring, they are not derived from the same source species and do not act sequentially in a metabolic pathway; and with the proviso that the non-natural product is not N-(E)-p-coumaroyl-3-hydroxyanthranilic acid or N-(E)-p-caffeoyl-3-hydroxyanthranilic acid. Further, a method for producing an active pharmaceutical ingredient by the aforementioned method and host cells for carrying out said methods are envisaged.

A versatile biosynthetic approach to amide bond formation

The development of versatile and sustainable catalytic strategies for amide bond formation is a major objective for the pharmaceutical sector and the wider chemical industry. Herein, we report a biocatalytic approach to amide synthesis which exploits the diversity of Nature's amide bond forming enzymes, N-acyltransferases (NATs) and CoA ligases (CLs). By selecting combinations of NATs and CLs with desired substrate profiles, non-natural biocatalytic pathways can be built in a predictable fashion to allow access to structurally diverse secondary and tertiary amides in high yield using stoichiometric ratios of carboxylic acid and amine coupling partners. Transformations can be performed in vitro using isolated enzymes, or in vivo where reactions rely solely on cofactors generated by the cell. The utility of these whole cell systems is showcased through the preparative scale synthesis of a key intermediate of Losmapimod (GW856553X), a selective p38-mitogen activated protein kinase inhibitor.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Efficient synthesis of new N-benzyl- or N-(2-furylmethyl)cinnamamides promoted by the 'green' catalyst boric acid, and their spectral analysis

New N-benzyl- or N-(2-furylmethyl)cinnamamides were prepared in good to excellent yields by amidation reactions between cinnamic acid and benzylamines or (2-furylmethyl)amine in the presence of 5 mol% boric acid. All the cinnamamides were characterized by IR and 1H and 13C NMR spectroscopy. Georg Thieme Verlag Stuttgart.

Practical and efficient synthesis of (E)-α,β-unsaturated amides bearing (S)-α-methylbenzylamine from 2-phosphonamides via Horner-Wadsworth-Emmons reaction

The highly stereoselective synthesis of (E)-α,β-unsaturated amides bearing (S)-α-methylbenzylamine was achieved from 2-phosphonamides via Horner-Wadsworth-Emmons reaction. The starting phosphonamides are easily prepared in two steps with excellent yields

First asymmetric aminohydroxylation of acrylamides

The first examples of the asymmetric aminohydroxylation of acryl amides are reported. This was accomplished with chiral acrylamides as substrates, which undergo diastereoselective oxidative transformation within the so-called 'second catalytic cycle' with diastereomeric excesses reaching 100:0. The reaction relies solely on the stereochemical information provided by the enantiomerically pure starting materials. A stereochemical model for the observed asymmetric induction is provided.

Highly efficient diastereoselective exo Diels-Alder reactions of homochiral 2-(N-acylamino)-1-thia-1,3-dienes: A powerful entry into optically pure thiopyrans

4-Phenyl-2-N-(R-(-)-α-(2-naphthyl)ethylamino)-1-thia-1,3-dienes when activated by acetyl chloride, undergo extremely efficient diastereoselective exo Diels-Alder cycloadditions giving access to thiopyrans of high optical purity.