Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

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Date

2023-08

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

A rapid and highly practical one-flask procedure for the positionally selective preparation of (acyloxy)methyl N-(2-hydroxybenzyl)iminodiacetate and related diesters from iminodiacetic acid and phenols is described. The key to this multicomponent phenol-Mannich condensation resides in the use of cesium iminodiacetate as the reaction partner. This protocol has been applied in an unusually direct synthesis of the intracellular fluorescent dye Calcein blue AM, for which scant experimental and spectroscopic data are presently available.

Description

This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.joc.3c00155

Keywords

base-catalyzed, cesium iminodiacetate, calcien blue AM, acyloxymethyl esters

Citation

Logan D. Mikesell and Tom Livinghouse The Journal of Organic Chemistry 2023 88 (16), 12064-12068 DOI: 10.1021/acs.joc.3c00155
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