40478-40-8

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InChI:InChI=1/C17H19NO/c1-14(16-10-6-3-7-11-16)18-17(19)13-12-15-8-4-2-5-9-15/h2-11,14H,12-13H2,1H3,(H,18,19)

Upstream product

• 618-36-0 rac-methylbenzylamine 
• 645-45-4 hydrocinnamic acid chloride 
• 26560-90-7 tetrakis(1,1,1,3,3,3-hexafluoro-2-propoxy)silane 
• 338-39-6 tetrakis(2,2,2-trifluoroethoxy)silane 
• 512-92-5 tetrakis(2,2,3,3,4,4,4-heptafluorobuthoxy)silane 
• 501-52-0 3-Phenylpropionic acid 
• 613-91-2 acetophenone oxime 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 710-11-2 2-oxo-4-phenylbutyric acid 
• 69932-21-4 4-hydroxyphenyl 3-phenylpropanate 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 19261-37-1 2-chloro-3-phenyl-propionaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 

Relevant academic research and scientific papers

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines

Strategies for the formation of amide bonds, that is, one of the most basic and important transformations in organic synthesis, have so far focused predominantly on dehydration reactions. Herein, we report and demonstrate the practical utility of a novel decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.

An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines

We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.

Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles

The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.

A two-step, one pot preparation of amines via acyl succinimides. Synthesis of the calcimimetic agents cinacalcet, NPS R-467, and NPS R-568

Abstract A method has been developed for the preparation of amines through a process of coupling acyl succinimides derived from commercially available carboxylic acids with amines to afford the corresponding amides. These amides are then reduced in situ with either diisobutylaluminum hydride or lithium aluminum hydride. The reaction tandem of the coupling reaction followed by the reduction affords the amine in fair to good yields after purification by flash chromatography. This one-pot, two reaction tandem process has been successfully applied to the synthesis of the calcimimetic agents cinacalcet, NPS R-467, and NPS R-568.

FENDILINE DERIVATIVES AND METHODS OF USE THEREOF

Disclosed herein are novel derivatives of fendiline, including compounds of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising these derivative compounds. Methods and intermediates useful for making the derivatives, and methods of using the derivatives, for example, for the inhibition of K-Ras plasma membrane localization, and compositions thereof, including for the treatment of cancer, are also provided.

Pseudomonas stutzeri lipase: A useful biocatalyst for aminolysis reactions

The use of Pseudomonas stutzeri lipase (PSL) as a biocatalyst for aminolysis reactions with bulky substrates has been investigated. PSL compared favorably to Novozym 435 (immobilized Candida antarctica lipase B, NOV435) in the aminolysis of various bulky methyl esters and amines. While NOV435 demonstrated a higher rate of aminolysis with methyl 2-phenylpropionic acid as the acyl donor, PSL outperformed NOV435 with secondary amines as the nucleophile. Methanol inhibition and a low affinity for bulky acyl donors were found to be the two main reasons for relatively low rates in the PSL-catalyzed aminolysis reactions. It was demonstrated that the use of molsieve 4A had a significant effect on the aminolysis rate and amide yield, since it enabled the effective removal of the inhibiting methanol from the reaction mixture.

Highly efficient method for the synthesis of carboxamides from carboxylic acids and amines using pyridine-3-sulfonyl chloride (3-PSC)

The use of pyridine-3-sulfonyl chloride (3-PSC) in dehydrating condensation was investigated. This novel reagent was successfully employed as a mild dehydrating reagent for preparing various carboxamides in good to excellent yields from the corresponding carboxylic acids and amines. Copyright

A versatile, practical, and inexpensive reagent, pyridine-3-carboxylic anhydride (3-PCA), for condensation reactions

A highly useful method for the preparation of carboxylic esters and carboxamides from various carboxylic acids was established by using a novel condensing reagent, pyridine-3-carboxylic anhydride (3-PCA), in the presence of 4-(dimethylamino)pyridine as an activator. The reactions of various carboxylic acids with nucleophiles, such as alcohols or amines, afforded the corresponding carboxylic acids or carboxamides in good to high yields under mild conditions by using simple experimental procedure. In addition, it was confirmed that this protocol was applicable to a gram-scale synthesis and the by-products, including pyridine-3-carboxylic acid and pyridine-3-carboxylate (or pyridine-3- carboxamide) produced in situ, were easily removed by using a simple aqueous workup.

Highly efficient method for the synthesis of carboxamides from carboxylic acids and amines using benzenesulfonic anhydride (BSA)

A highly efficient method by using benzenesulfonic anhydride (BSA) in the presence of 4-(dimethylamino)pyridine (DMAP) to synthesize carboxamides from various carboxylic acids and amines including sterically hindered ones is established. This reaction proceeds smoothly to provide the desired product in high yield. Copyright