What is di-tert-butyl dicarbonate used for in peptide synthesis?

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. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis.

How do you recrystallize di-tert-butyl dicarbonate?

(64–75%, (Note 7)) of di-tert-butyl tricarbonate as a colorless solid. This crude product is recrystallized by dissolving it in 1250 ml. of pentane at room temperature, and cooling the solution to −15°.

How do I get rid of excess Boc2O?

After the reaction completed, the mixture was concentrated under reduced pressure to remove the acetone. Then excess Boc2O was removed by extracting with ether (3×30 mL), and the pH was adjusted to 3-4 with 2 N HCl in ice bath.

What is BOC Group in chemistry?

The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group (BOC group) is a protecting group used in organic synthesis. The BOC group can be added to the amine under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium carbonate (soda ash):

How do you quench BOC anhydride?

Boc anhydride (50.0 g, 229 mmol) was dissolved in 400 mL tetrahydrofuran and added to the solution of ethylenediamine via addition funnel over 45 min with vigorous stirring. After 18 h, the reaction was quenched by addition of 500 mL H2O.

What is the use of FMOC protecting group in organic synthesis?

Protection of Amino Groups New, stable amino-protecting reagents, Boc-DMT and Fmoc-DMT, were prepared, and found to be useful for the introduction of Boc and Fmoc groups into amines. Both the reagents can protect various amines including amino acids in good yield in aqueous media.

How do I uninstall TFA after Boc deprotection?

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.

What is protection and deprotection?

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 much TFA do I need for Boc deprotection?

4a (0.33 g, 0.25 mmol) was reacted following the general procedure for the deprotection of the Boc-group. TFA (3.0 mL), CH2Cl2 (6.0 mL). The product was used without further purification.

Can triethylamine remove Fmoc?

The Fmoc group is, in general, rapidly removed by primary (i.e., cyclohexylamine, ethanolamine) and some secondary (i.e., piperidine, piperazine) amines, and slowly removed by tertiary (i.e., triethylamine [Et3N], N, N-diisopropylethylamine [DIEA]) amines.

Why is Fmoc a good protecting group?

Fmoc protection has found significant use in solid phase peptide synthesis (SPPS), because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin. A typical SPPS Fmoc deprotection is performed with a 20% solution of piperidine in N,N-dimethylformamide.

How do you remove TFA from peptides?

TFA and HCl are both strong acids that will protonate any amino group. They can be removed by performing anion exchange on the same reversed phase HPLC on which the peptide was purified.

What are the reactions of di-tert-butyl dicarbonate?

Di-tert-butyl dicarbonate and 4- (dimethylamino)pyridine revisited. Their reactions with amines and alcohols Activation of carboxylic acids by pyrocarbonates. Synthesis of symmetric anhydrides and esters of N-protected amino acids using dialkyl pyrocarbonates as condensing reagents Activation of carboxylic acids by pyrocarbonates.

What can be done with di-tert-butyl dicarb?

Di-tert-butyl dicarb… Activation of a carboxy group by dialkyl pyrocarbonates. Synthesis of symmetrical anhydrides and aryl esters of N-protected amino acids using di-tert-butyl pyrocarbonate as condensing reagent

How much does di tert butyl dicarbonate weigh?

Di-tert-butyl dicarbonate PubChem CID 90495 Synonyms Di-tert-butyl dicarbonate 24424-99-5 BOC Molecular Weight 218.25 Date s Modify 2021-06-19 Create 2005-03-27

When to use di-tert-butyl anhydride as a reagent?

Di-tert-butyl dicarbonate (Boc anhydride) can be used: As a reagent to introduce Boc protecting group for the amine functionalities. To prepare tert -butyl ethers and Boc-alcohols in presence of Lewis acid catalyst. As a carboxylating agent for the preparation of a variety of tert -butyl carboxylates.