79919-40-7

Upstream product

• 106-31-0 butanoic acid anhydride 
• 618-36-0 rac-methylbenzylamine 
• 141-75-3 butyryl chloride 
• 110-69-0 butyraldehyde oxime 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 638-11-9 isopropyl butyrate 
• 107-92-6 butyric acid 
• 105-54-4 butanoic acid ethyl ester 
• 98-86-2 acetophenone 
• 541-35-5 butanamide 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 

Downstream Products

• 5412-64-6 butyl-(1-phenyl-ethyl)-amine 
• 19302-34-2 (S)-(-)-N-(1-phenylethyl)butylamine 
• 628729-62-4 (R)-(+)-N-butyl-N-(α-phenylethyl)amine 

Relevant academic research and scientific papers

Rapid synthesis of aliphatic amides by reaction of carboxylic acids, grignard reagent and amines: Application to the preparation of [11C]amides

Aliphatic amides have been prepared in moderate to good yields (30-70%) by treatment in THF of magnesium halide carboxylates with amines in the presence of 2.5 equivalents of alkylmagnesium halide. The reaction is rapid (30 min) and has been successfully

Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones

A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete

9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis

A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy-to-access 9-silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization.

Solvent-free kinetic resolution of primary amines catalyzed by Candida antarctica lipase B: Effect of immobilization and recycling stability

Highly enantioselective (E >200) N-acylation of nine racemic primary amines with isopropyl methoxyacetate in the presence of Candida antarctica lipase B (Novozym 435) has been reported to yield the unreacted (S)-amines (ee ≥98%) and produced the (R)-amides (ee ≥95%) at 50% conversion under solvent-free conditions. One of the amines and the acyl donor have been used in an equimolar ratio at room temperature (23 °C). Under the reaction conditions, the reuse stability of Novozym 435 with 1-phenylethylamine (as a model compound) has been shown to be poor while somewhat improved stability has been observed with an in-house prepared sol-gel CAL-B catalyst.

Catalytic acylation of amines with aldehydes or aldoximes

The simple nickel salt NiCl2?6H2O catalyzes the coupling of aldoximes with amines to give secondary or tertiary amide products. The aldoxime can be prepared in situ from the corresponding aldehyde. The use of 18O-labeled oximes has allowed insight into the mechanism of this reaction.

Fully enzymatic resolution of chiral amines: Acylation and deacylation in the presence of Candida antarctica lipase B

A fully enzymatic methodology for the resolution of chiral amines has been demonstrated. Candida antarctica lipase B (CaLB)-catalyzed acylation with N-methyl-and N-phenylglycine, as well as analogues having the general formula R1-X-CH2CO2R2 (R1 = Me, Ph; X = O, S) afforded the corresponding enantioenriched amides, which were subsequently enzymatically hydrolyzed. Surprisingly, CaLB also proved to be the catalyst of choice for this latter step. The heteroatom in the acyl donor profoundly influences both the enzymatic acylation and deacylation; the O-substituted reagents performed best with regard to enantioselectivity as well as reaction rate in synthesis and hydrolysis.

Lipase-catalyzed synthesis of chiral amides. A systematic study of the variables that control the synthesis

A systematic study of the aminolysis of esters catalyzed by different lipases from different origins was carried out. A factorial analysis showed that the main variables that control the amide synthesis are: temperature, hydrophobicity of the solvent, reaction volume and amount of water added to the reactor medium. Besides, several undescribed interactions of variables are significative in the control of the process, too. The resolution of racemic esters or amines was analyzed. Lipascs from Rhizopus niveus, Candida antarctica B and PPL gave the best enantioselectivities in the resolution of chiral esters while C. rugosa and P. cepacia lipases were the less interesting lipases. α-Chymotrypsin shows lower enantioselectivity and yield than Rhizopus niveus, C. antarctica B and PPL lipases in the resolution of racemic esters. This protease needs a large excess of acyl donor in respect to the amine and works at a lower temperature than lipases due to its low thermostability. Ail the tested lipases showed R-enantiopreference in the aminolysis of esters using (R,S) 1-phenyl-ethylamine. In this reaction, the lipase A from C. antarctica, (SP526) and Rhizopus niveus lipase are good catalysts for the synthesis. On the other, PS and PPL are less interesting biocatalysts. Therefore, the optimum biocatalyst is different if we want to resolve (R,S) esters or (R,S) amines. The aminolysis is interesting for the resolution of racemic amines but not for the resolution of racemic esters. The immobilization does not alter the enantiopreference of the lipases.

Chiral Aggregation Phenomena. 3. Chiral Discrimination in the Monolayer Packing of N-(α-Methylbenzyl)stearamides on Aqueous Acid Subphases: Thermodynamic Behavior

The study of monolayers at the air-liquid interface offers unusual opportunities to investigate the effects of stereochemical factors in organized systems.As a first step toward developing this field, we have examined some surface properties of N-(α-methy