What is BOC deprotection?

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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. Concentrated hydrochloric acid, or trifluoroacetic acid (TFA) are the acids of choice.

How is BOC removed?

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.

Why is BOC a good protecting group?

The Boc group is stable towards most nucleophiles and bases. Therefore, an orthogonal protection strategy using a base-labile protection group such as Fmoc is possible. Scavengers such as thiophenol may prevent nucleophilic substrates from being alkylated.

How do you quench a TFA?

To remove traces of TFA you can use exsiccator with KOH and – optionally – some heat. If you have the salt with TFA you could dissolve your product in water add some NH3 – until you have slight alkalline conditions – and extract your product with CHCl3 or DCM, evaporate and dry over KOH. Regards.

For what purpose is Boc used?

tert-Butyloxycarbonyl (Boc) is a protecting group often used in the synthesis of organic compounds. Boc is specifically used to protect amine in the solid phase synthesis of peptides (Green, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, Wiley-Interscience: New York, 1999, pp 518-525, 736-739).

Is Boc water soluble?

Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis….Di-tert-butyl dicarbonate.

Boiling point 56 to 57 °C (133 to 135 °F; 329 to 330 K) (0.5 mmHg)
Solubility in water Insoluble
Solubility in other solvents Soluble in most organic solvents

Can Boc protect alcohols?

Hello, Boc protection of secundary amine in presence of primary alcohol works perfect.

How can we protect 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 TFA?

TFA means “Thanks for Asking.”

What is Diboc?

Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride.

How do you get rid of Boc anhydride?

Protection of the amine can also be accomplished in acetonitrile solution using 4-dimethylaminopyridine (DMAP) as the base. 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.

How can we protect alkenes?

The presence of a bromide substituent, instead of a hydrogen or methyl group, on a carbon–carbon double bond, protects the alkene from addition reactions when exposed to trifluoroacetic acid.

How to do work up of Boc deprotection reaction?

I have a problem during work-up with ethyl acetate. It starts coagulation during addition of brine solution into ethyl acetate. Join ResearchGate to ask questions, get input, and advance your work.

Which is the best way to deprotecte a water soluble compound?

This method we used to do for water soluble compound which is having inorganic salts. also try the boc deprotection in 1M HCL/Ethyl acetate 1:1 mixture stirring at room temperature. after reaction is complete just vacc it down and it is done.

What kind of reagents are used for deprotection?

Two other common deprotection methods avoid the use of a strong acid. They can be useful for acid-labile compounds. The trade off is a slightly more complex reaction set up and longer reaction times, up to 48-72h. The two reagents that can be used are trimethylsilyl iodide (TMSI) and zinc bromide.

How to remove protected amine from DCM solvent?

Dissolve the protected amine in DCM, add an excess of zinc bromide (2-3 equivalents), or TMSI (1.2-1.5 equivalents added dropwise), stir at room temperature overnight. Isolate the product by removing the solvent under vacuum. Wuts, Peter G. M.; Greene, Theodora W. “Protection for the Amino Group”.

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