A mild procedure for the clay catalyzed selective removal of the tert-butoxycarbonyl protecting group from aromatic amines. Selective removal of the tert-butoxycarbonyl group from secondary amines: ZnBr 2 as the deprotecting reagent. Selective synthesis of carbamate protected polyamines using alkyl phenyl carbonates. Pittelkow, M., Lewinsky, R., Christensen, J.B. Environmentally benign N-Boc protection under solvent-and catalyst-free conditions. Jia, X., Huang, Q, Li, J., Li, S., Yang, Q. Montmorillonite K10 clay in ClCH 2CH 2Cl selectively cleaves aromatic N-BOC groups, leaving aliphatic N-BOC amines intact.ZnBr 2 in CH 2Cl 2 selectively cleaves secondary N-BOC groups, leaving primary N-BOC groups untouched.One way to selectively protect primary amines in polyamines is to use t-BuOCO 2Ph in CH 2Cl 2, or DMF.The BOC group can also be added without the use of a solvent.Organic Process Research & Development, 8 (6), 945947 10.1021/op049842z sci hub to open science save Coffey, D. Reagents: Strong Organic Acid (TFA, p-Toluenesulfonic Acid), DCM Sci-Hub Large Scale Deprotection of atert-Butoxycarbonyl (Boc) Group Using Aqueous HCl and Acetone.Type of Reaction: Nucleophilic Acyl Substitution.Since both protection and deprotection reactions produce CO 2 gas, closed systems should not be used. The libraries were subsequently washed extensivly with DCM and DMF before being. The protected amine is first protonated by TFA, triggering the production of a t-butyl cation and carbamic acid, which is decarboxylated to yield the amine. The final Boc-deprotection of the Boc- yAbu residue was then carried out. For preceding exam- ples of high-temperature Boc deprotection in flow and its application in multistep reaction sequences, see: A. Of all the cleavage procedures HF appears to be the most versatile and least harmful to a wide variety of peptides synthesized on Boc-based resins. Roubila Belghiche (1) orcid, Zinelaabidine Cheraiet (2,). Trifluoroacetic acid (TFA) and dichloromethane (DCM) are commonly used to remove the BOC group. Boc Resin Cleavage and Deprotection The most popular reagent for cleavage of peptides from Boc-based resins is anhydrous HF. Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst. The base then abstracts a proton from the positively charged amine. The amine attacks a carbonyl site of BOC 2O, creating a t-butyl carbonate leaving group that breaks down to carbon dioxide gas and t-butoxide. The scope of this procedure is explored for the deprotection of a variety of amines including amino acid derivatives. The BOC (tert-butoxycarbonyl) group is used to protect amines in synthetic reactions, is probably the most common amine protecting group in non-peptide chemistry.ĭi-tert-butyl dicarbonate, BOC 2O (also known as di-tert-butyl pyrocarbonate or BOC anhydride), triethylamine (TEA), and tetrahydrofuran (THF) are commonly used to add the BOC group. A mild and efficient procedure is described for the removal of the tert -butoxycarbonyl (BOC) group using boron trifluoride etherate and molecular sieves in dichloromethane at room temperature.