Synthesis of amides

Beckwith, A. L. J.

doi:10.1002/9780470771235.ch2

Cited by 49 publications

(34 citation statements)

References 553 publications

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“…the spontaneous chemical acylation of the amine by the carboxylic ester of arginine occurred (72% C 3 (LA) yield). It is noteworthy that this reaction took place under mild temperature conditions and without any catalyst, which is not common with simple amino acid alkyl esters and weak amine bases (Beckwith, 1970;Matsumoto et al, 1989). Nonetheless, the chemical acylation in solution gave only practical yields at 1,3-diaminopropane/LAE mole ratio above 2.5.…”

Section: Two-step Synthesismentioning

confidence: 96%

Chemo-enzymatic synthesis of arginine-based gemini surfactants

Piera¹,

Infante²,

Clapés³

2000

Biotechnol. Bioeng.

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Section: Two-step Synthesismentioning

confidence: 96%

Chemo-enzymatic synthesis of arginine-based gemini surfactants

Piera¹,

Infante²,

Clapés³

2000

Biotechnol. Bioeng.

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“…The reaction with the free amines probably journeys across the well-known tetrahedral intermediate 47 and, therefore, does not involve the thiocarbonyl function. In cases where steric demand was negligible, the free amines mimicked the reaction time, yield, and enantiomeric excesses obtained with the corresponding benzenesulfenamides.…”

Section: Scheme 16mentioning

confidence: 99%

New Reactions of the Thiocarbonyl Function. The Synthesis of Hindered Peptides

Barton

Ferreira

1997

Phosphorus, Sulfur, and Silicon and the Related Elements

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The well-known radical chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of Nhydroxypyridine-2(l//)-thione (a Barton PTOC ester) and a sulfenamide. The atomeconomical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected dipeptides. The oxidation-reduction technology pertaining to the disulfide-phosphine combination facilitated the generation of transient Barton PTOC esters. In conjunction with the appropriate benzenesulfenamide, the Barton PTOC ester of benzoyl-L-leucine was shown to preserve optical integrity according to the sensitive Young test, albeit at low temperature. However, the thermodynamic forces at play are powerful and, as a result, the yields were not compromised. In all but the sterically demanding instances, the parent free amine almost matched the reaction time, yield, and enantiomeric excess of the corresponding benzenesulfenamide in its reaction with a Barton PTOC ester.

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“…4 Numerous methods have been reported for the preparation of carboxamides in the literature using conventional methods by coupling of carboxylic acid derivatives or acyl halides, anhydrides, aldehydes and alcohols with amines. 5,6 In a report by Galat and Elion shows, aliphatic or aromatic amines were conveniently acylated using hydroxylammonium hydrochloride salts. 7 4 , lanthanides, polymer-bound HfCl 4 and many more.…”

Section: Introductionmentioning

confidence: 99%