Aqueous Phosphoric Acid as a Mild Reagent for Deprotection of tert-Butyl Carbamates, Esters, and Ethers

Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbama...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 71; no. 24; pp. 9045 - 9050
Main Authors:	Li, Bryan, Berliner, Martin, Buzon, Richard, Chiu, Charles K.-F, Colgan, Stephen T, Kaneko, Takushi, Keene, Nandell, Kissel, William, Le, Tung, Leeman, Kyle R, Marquez, Brian, Morris, Ronald, Newell, Lisa, Wunderwald, Silke, Witt, Michael, Weaver, John, Zhang, Zhijun, Zhang, Zhongli
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 24-11-2006
Subjects:	Carbamates - chemistry Chemistry Esters - chemistry Ethers - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Indicators and Reagents - chemistry Magnetic Resonance Spectroscopy Organic chemistry Phosphoric Acids - chemistry Preparations and properties Water Phosphoric acid Acetic acid esters Ether Mild operating conditions Nitrogen heterocycle Deprotection Phenyl ether Lactone Selectivity Stereochemistry Oxygen heterocycle Organic carbamate Ketone Acetal Ester Benzylic compound Cyclic compound Azetidine derivatives Chemical synthesis
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Summary:	Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative 4, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.
Bibliography:	ark:/67375/TPS-V6Z1KTP7-4 istex:C2A901C9C419ADA74FBA0208C1FE9A5790B5B75B ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo061377b