Preparation and use of 2-t-butoxyphenol for the synthesis of monoaminoacyl catechol derivatives

Mitchell, Alexander R.; Rahman, A. U.; Merrifield, R. B.

doi:10.1007/978-94-011-3034-9_11

Cited by 2 publications

(7 citation statements)

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“…The 2- tert -butoxyphenol 3 may be prepared in large quantities from catechol by the route shown in Scheme , this being a modification of Merrifield's method ) with diazotized 4-amino benzene sulfonic acid gave a water-soluble azo derivative that, in situ, was reduced with sodium dithionite to give the amine 4 .…”

Section: Resultsmentioning

confidence: 99%

“…Cowell and Jones and Merrifield et al . have both, therefore, explored protected o -hydroxyphenyl esters as safety catch linkers. The first group used the benzyloxyphenyl ester and released the free phenol by hydrogenolysis, while Merrifield used the tert -butoxyphenyl ester and activated proteolytically with trifluoroacetic acid (TFA).…”

Section: Introductionmentioning

confidence: 99%

“…The first group used the benzyloxyphenyl ester and released the free phenol by hydrogenolysis, while Merrifield used the tert -butoxyphenyl ester and activated proteolytically with trifluoroacetic acid (TFA). He also made mention of application of these latter esters in cyclic peptide synthesis on solid phase, but with no great success and with no details given of the type of linker employed …”

Section: Introductionmentioning

confidence: 99%

“…Conversely, the introduction of o-hydroxy groups into aryl esters increases the reactivity by some degree due to anchimeric assistance of the hydroxy group during reaction with nucleophiles, possibly by stabilization of the tetrahedral intermediate. Cowell and Jones 10 and Merrifield et al 11 have both, therefore, explored protected o-hydroxyphenyl esters as safety catch linkers. The first group used the benzyloxyphenyl ester and released the free phenol by hydrogenolysis, while Merrifield used the tert-butoxyphenyl ester and activated proteolytically with trifluoroacetic acid (TFA).…”

Section: Introductionmentioning

confidence: 99%

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The Preparation of a New “Safety Catch” Ester Linker for Solid-Phase Synthesis

et al. 2001

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A new “safety catch” linker for esters has been synthesized on polystyrene resin. This 2-tert-butoxyphenol resin 10 may be acylated to give a relatively stable ester that will allow nucleophilic chemistry without reaction at the linking ester group. Removal of the tert-butyl group with acid unmasks a highly reactive 2-hydroxyphenyl ester that reacts readily with nucleophiles to cause release of the product from the resin. This sequence has been exemplified by acylating the resin with various bromo acids, carrying out nucleophilic displacements with thiols, phenols, or amines, activating the ester with trifluoroacetic acid and cleaving from the resin with amines to give the (nucleophile) substituted carboxamides in high yield and purity. Kinetic studies with a model ester revealed half-lives for reaction with morpholine of 119 h for the tert-butoxyphenyl ester and 1 min for the corresponding phenol.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Preparation of a New “Safety Catch” Ester Linker for Solid-Phase Synthesis

et al. 2001

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“…35 This allows the preparation of peptidyl-catechol derivatives 25 for use in cyclization studies ( Figure 10). 37 Jones, in later reports, also recognized the sluggish reactivity of o-hydroxyphenyl esters when compared with ordinary active esters (p-nitrophenyl, pentachlorophenyl, or succinimido), especially in dipolar aprotic solvents (DMF, DMSO) where aminolysis is even retarded somewhat. 38,39 Suffice it to say that the cyclic peptide project that I brought to New York became inordinately time consuming (when to stop?…”

Section: Catechol Supportsmentioning

confidence: 99%

Studies in solid‐phase peptide synthesis: A personal perspective

Mitchell

2008

Biopolymers

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By the early 1970s it had became apparent that the solid‐phase synthesis of ribonuclease A could not be generalized. Consequently, virtually every aspect of solid‐phase peptide synthesis (SPPS) was reexamined and improved during the decade of the 1970s. The sensitive detection and elimination of possible side reactions (amino acid insertion, Nα‐trifluoroacetylation, Nαϵ‐alkylation) were examined. The quantitation of coupling efficiency in SPPS as a function of chain length was studied. A new and improved support for SPPS, the “PAM‐resin,” was prepared and evaluated. These and many other studies from the Merrifield laboratory and elsewhere increased the general acceptance of SPPS leading to the 1984 Nobel Prize in Chemistry for Bruce Merrifield. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90:215–233, 2008.This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprintversion. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

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Preparation and use of 2-t-butoxyphenol for the synthesis of monoaminoacyl catechol derivatives

Cited by 2 publications

References 2 publications

The Preparation of a New “Safety Catch” Ester Linker for Solid-Phase Synthesis

The Preparation of a New “Safety Catch” Ester Linker for Solid-Phase Synthesis

Studies in solid‐phase peptide synthesis: A personal perspective

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