What is BOC deprotection?

The deprotection of a BOC-protected amine is a simple carbamate hydrolysis in acidic conditions. The starting material is dissolved in water or organic solvent, such as toluene, dichloromethane, or ethyl acetate. Two other common deprotection methods avoid the use of a strong acid.

How do you Deprotect a Boc group?

Removal of the BOC in amino acids can be accomplished with strong acids such as trifluoroacetic acid in dichloromethane, or with HCl in methanol. A complication may be the tendency of the t-butyl cation intermediate to alkylate other nucleophiles; scavengers such as anisole or thioanisole may be used.

What is a deprotection reaction?

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. This step is called deprotection.

How is the triisopropylsilyl group desilylated by TBAF?

However, acylation with acetic anhydride using BF 3 -etherate as catalyst gave 2-acyl-1-phenylsulfonylpyrrole, 48 which on basic hydrolysis produced 2-acylpyrrole. In the case when the N -substituent is the triisopropylsilyl group, it was desilylated by TBAF.

Which is the best method for deprotection of acetylenes?

However, the procedures for deprotection of TIPS- acetylenes are few. One method, reported by Kim, uses 1.5 equiv. of AgF to remove the TIPS group in acetylenes contain- ing another functional group (alkene, ester, ether, alcohol and, in one example, the ketal of an aminoalcohol). Another method reported by Fallis [18] employs Cu(OAc) 2and Bu

Which is the best catalyst for BN deprotection?

The Bn protecting group is selectively cleaved by Pd-catalysed hydrogenolysis. The reaction can be performed in numerous solvents under 1-3 bar H 2 and moderate heat. The catalyst of choice is 10% Pd/C. As there is no need for high hydrogen pressure, standard laboratory glassware can be used.

How are BOC protected amino groups used in chemoselective esterification?

Boc-Protected Amino-Groups in Multi-step Syntheses SmCl 3 is an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive hydroxyl protecting groups such as Boc, THP, and TBDMS. Chemoselective deprotection is demonstrated through suitable examples.