A simple and mild esterification method for carboxylic acids using mixed carboxylic-carbonic anhydrides

Kim, Sunggak; Lee, Jae-In; Kim, Youn Chul

doi:10.1021/jo00205a004

Cited by 134 publications

(58 citation statements)

References 2 publications

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“…35 The advantage of our method is simultaneous protection of phenolic hydroxyl group(s) on phenolic acid in the esterification and amidation. A one-pot esterification of N-protected amino acids using isopropenyl chloroformate has been reported by Jouin et al 36 In the report, the esterification is described as being inadaptable to preparation of esters with free hydroxyl group on amino acid side chain.…”

Section: Resultsmentioning

confidence: 99%

One-pot esterification and amidation of phenolic acids

et al. 2014

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Section: Resultsmentioning

confidence: 99%

One-pot esterification and amidation of phenolic acids

et al. 2014

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“…We synthesized ( R )- 32 from ( R )- 29 6 using a mild esterification method 25 that employed benzylchloroformate in the presence of base and catalytic amounts of 4-dimethylaminopyridine (DMAP) (Scheme 4). Subsequent TFA deprotection of ( R )- 32 gave PAAD ( R )- 10 .…”

Section: Resultsmentioning

confidence: 99%

Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

et al. 2011

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Primary Amino Acid Derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to Functionalized Amino Acids (FAAs) (N′-benzyl 2- substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogs of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).

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“…As unprotected amino acids are usually difficult to purify, we have started our research with fully protected amino acid (S)-3c. The latter was synthesized from N-benzyloxycarbonyl-L-22 azidohomoalanine ((S)-3b) and CbzCl via decarboxylative benzylation procedure in 69% yield (Scheme 1) [24].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Enantiomerically Enriched 1,2,3- Triazole-derivatized Homoalanines

Turks

Strelnikova

Kumpiņš

et al. 2013

Material Science and Applied Chemistry

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Abstract. In recent decades, the synthesis of amino acidtriazole conjugates has become an emerging area. L-and Dazidohomoalanine derivatives readily undergo copper(I)-catalyzed azide-alkyne dipolar cycloaddition reaction. The expected 4-substituted-1H-1,2,3-triazol-1-yl-homoalanines are obtained in the reactions of either N-and O-protected or protecting-group-free azidohomoalanines with various alkynes. 1,2,3-Triazole conjugate formation tolerates various functional groups. The synthetic approach that uses N-and O-protected starting materials relays on the standard chromatographic purification of intermediates that are further deprotected by hydrogenolysis. In this way, the purification of final products is not required. The synthetic approach that uses protecting-groupfree azidohomoalanine is faster from a synthetic point of view as it includes only one step. However, the purification of protectinggroup-free amino acid derivatives is laborious. Additionally, we have shown that the chiral stationary phase CROWNPAK ® CR(+), which is based on chiral crown ether as a selector, is applicable for direct chromatographic determination of enantiomeric ratio of the title products.

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A simple and mild esterification method for carboxylic acids using mixed carboxylic-carbonic anhydrides

Cited by 134 publications

References 2 publications

One-pot esterification and amidation of phenolic acids

One-pot esterification and amidation of phenolic acids

Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N′-Benzyl 2-Amino-3-methylbutanamide

Synthesis of Enantiomerically Enriched 1,2,3- Triazole-derivatized Homoalanines

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