Lipase-Catalyzed Syntheses of N-Octyl-Alkylamides in Organic Media

Tuccio, Béatrice; Ferre, E.; Comeau, Louis-Claude

doi:10.1016/0040-4039(91)85079-k

Cited by 32 publications

(26 citation statements)

References 4 publications

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“…The catalyst loading was 1.44 mg immobilized enzyme to 1 mmol substrate using a slight excess of the aqueous hydroxylamine (1.24 equiv). 48 It was found that the reaction 30 performed equally well with T. lanuginosus lipase immobilized on Accurel EP 100 as catalyst. Furthermore, Obenzylhydroxylamine, as well as different hydrazines could be used as coupling partners to form the corresponding carboxylic derivatives in excellent yields in t-butanol at 40 ºC (Scheme 11).…”

Section: Hydroxamic Acids and Acyl Hydrazinesmentioning

confidence: 95%

“…The first report on the enzymatic formation of secondary amides was published in 1991 by Tuccio et al 30 A series of carboxylic 10 acids were converted into the corresponding n-octylamides using Porcine pancreas lipase (PPL), Candida cylindracea lipase (CCL) and two mycelia preparations of Rhizopus arrhizus (RAL) and Penicillum cyclopium (PCL) with lipasic activity. The best result was obtained with RAL and palmitic acid (50% yield) at 40 15 ºC for 7 days with a 2:1 ratio of acid to amine, and a catalyst loading of 2000 lipasic units of enzyme to 1 mmol carboxylic acid.…”

Section: Secondary and Tertiary Amidesmentioning

confidence: 99%

“…3 Polymers 25 based on the amide linkage are of importance in a wide range of applications, from everyday materials such as nylons, to more advanced uses in drug delivery systems, adhesives and wound healing. 4 In addition, the amide bond is commonly found as a key structural element in agrochemicals and in products from the fine 30 chemicals industry.…”

Section: Introductionmentioning

confidence: 99%

“…13 For comparison, the structurally similar N-benzylphenylacetamide 25 was formed in only 13% yield or less, when phenylacetic acid and benzylamine were allowed to react in THF at 70 ºC at a concentration of 0.4 M and a reaction time of 24 hours. 15 The literature on thermal amidation is not covered in this review unless the non-catalysed reaction is specifically mentioned by the 30 authors. 35 …”

Section: Introductionmentioning

confidence: 99%

“…Rhizopus arrhizus lipase-catalysed amidation of 35 carboxylic acids of different chain lengths (Tuccio, 1991).…”

mentioning

confidence: 99%

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Catalytic amide formation from non-activated carboxylic acids and amines

et al. 2014

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The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing criterias for green 10 chemistry. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysis, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.

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Section: Hydroxamic Acids and Acyl Hydrazinesmentioning

confidence: 95%

Section: Secondary and Tertiary Amidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Rhizopus arrhizus lipase-catalysed amidation of 35 carboxylic acids of different chain lengths (Tuccio, 1991).…”

mentioning

confidence: 99%

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Catalytic amide formation from non-activated carboxylic acids and amines

et al. 2014

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Lipase and esterase-catalyzed acylation of hetero-substituted nitrogen nucleophiles in water and organic solvents

Hacking

Akkus

Rantwijk

et al. 2000

Biotechnol. Bioeng.

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Inverconversion of Nitriles, Carboxylic Acids, and Derivatives

Larock

Rozhkov

2018

Comprehensive Organic Transformations

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Carboxylic Acids to Acid Halides Carboxylic Acids to Acid Anhydrides Carboxylic Acids to Esters Carboxylic Acids to Amides Carboxylic Acids to Imides Carboxylic Acids to Nitriles Acid Halides to Other Acid Halides Acid Halides to Acid Anhydrides Acid Halides to Esters Acid Halides to Amides Acid Halides to Imides Acid Halides to Nitriles Acid Anhydrides to Acid Halides Acid Anhydrides to Esters Acid Anhydrides to Amides Acid Anhydrides to Imides Esters to Carboxylic Acids Esters to Acid Halides Esters to Acid Anhydrides Esters to Other Esters Esters to Amides Esters to Nitriles Amides to Carboxylic Acids Amides to Esters Amides to Other Amides Amides to Imides Amides to Nitriles Imides to Esters or Lactones Imides to Amides Imides to Other Imides Nitriles to Carboxylic Acids Nitriles to Esters Nitriles to Amides Other Interconversions

show abstract

Lipase-Catalyzed Syntheses of N-Octyl-Alkylamides in Organic Media

Cited by 32 publications

References 4 publications

Catalytic amide formation from non-activated carboxylic acids and amines

Catalytic amide formation from non-activated carboxylic acids and amines

Lipase and esterase-catalyzed acylation of hetero-substituted nitrogen nucleophiles in water and organic solvents

Inverconversion of Nitriles, Carboxylic Acids, and Derivatives

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