Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers
| Autor: | Chiu Charles K, Ronald Morris, Silke Wunderwald, Kyle R. Leeman, Richard A. Buzon, Tung Le, Nandell F. Keene, Takushi Kaneko, Zhongli Zhang, Lisa Newell, John D. Weaver, Stephen T. Colgan, Michael F. Witt, Brian L. Marquez, William Kissel, Bryan Li, Martin A. Berliner, Zhijun Zhang |
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| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Carbamate Aqueous solution Magnetic Resonance Spectroscopy medicine.medical_treatment Organic Chemistry Azetidine Water Esters chemistry.chemical_compound chemistry Reagent medicine Organic chemistry Indicators and Reagents Phosphoric Acids Carbamates Selectivity Phosphoric acid Derivative (chemistry) Lactone Ethers |
| Zdroj: | The Journal of organic chemistry. 71(24) |
| ISSN: | 0022-3263 |
| Popis: | 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, 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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