Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers

…, ST Colgan, T Kaneko, N Keene, W Kissel…

Index: 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 Journal of Organic Chemistry, 2006 , vol. 71, # 24 p. 9045 - 9050

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Citation Number: 52

Abstract

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 ...