How is the BOC group of an amino acid derivative removed?
Removal of the BOC in amino acids can be accomplished with strong acids such as trifluoroacetic acid neat or in dichloromethane, or with HCl in methanol.
What is BOC Group in chemistry?
The BOC (tert-butyloxycarbonyl) protecting group, chemically a di-tert-butyl dicarbonate (Boc2O), is probably the most common amine protecting group in non-peptide chemistry. The reaction conditions for the amine protection are quite flexible.
How can we protect carboxylic acids?
Protection of carboxylic acids: Methyl esters – Removed by acid or base. Benzyl esters – Removed by hydrogenolysis. tert-Butyl esters – Removed by acid, base and some reductants.
What is the first step in the mechanism for Boc removal?
The first step in the mechanism is to deprotect the molecule with an acid, trifluoroacetic acid (TFA). The mechanism begins with an acid catalyzed protonation of the oxygen attached to the tert-butyl group of the Boc protecting group on the secondary amine.
How do I uninstall TFA after Boc deprotection?
TFA can be removed using rotary evaporator. Add Methanol (5~6 times) and remove methanol by rotary evaporator. Most of the TFA is removed using this procedure and traces can be removed using vacuum.
What is carbamate group?
The carbamates are a group of insecticides that includes such compounds as carbamyl, methomyl, and carbofuran. They are rapidly detoxified and eliminated from animal tissues. Their toxicity is thought to arise from a mechanism somewhat similar to that for the organophosphates.
Do protecting groups work on carboxylic acids?
Carboxylic acid protecting groups Protection of carboxylic acids: Methyl esters – Removed by acid or base. Benzyl esters – Removed by hydrogenolysis. tert-Butyl esters – Removed by acid, base and some reductants.
What is the purpose of the Boc protecting group in organic chemistry?
Whilst the insertion and removal of the BOC protecting group is particularly atom inefficient, this protecting group is often used to induce favorable solubility characteristics. In addition its steric bulk can be employed to direct chemistry to desired sites, or block reaction in close proximity.
What is the role of BOC in amine protection?
The tert-butyloxycarbonyl (Boc) group is used as a protecting group for amines in organic synthesis. Common amine protection methods. Simple rapid stirring of a mixture of the amine and di-tert-butyl dicarbonate (Boc 2O) suspended in water at ambient temperature, an example of an on-water reaction.
What solvents are used in BOC deprotections?
Many BOC deprotections are carried out in chlorinated solvents like dichloromethane, or 1,4-dioxan which should be minimised or replaced wherever possible. Protecting Groups.
What is the use of BOC in the pharmaceutical industry?
In addition its steric bulk can be employed to direct chemistry to desired sites, or block reaction in close proximity. Also, removal of BOC under mild conditions makes it useful where orthogonal protecting group strategy is required. Many amine / amino acid /peptide synthons supplied to the pharma industry are sold BOC protected.