What is BOC functional group?
The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group (BOC group) is a protecting group used in organic synthesis. Removal of the BOC in amino acids can be accomplished with strong acids such as trifluoroacetic acid in dichloromethane, or with HCl in methanol.
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 do 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.
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).
How do I remove tert-butyl group?
The catalyst is easily recovered and reused several times without loss of activity. In addition, the tert-butyl group is removed very quickly from alcohols and phenols in methanol in the presence of Er(OTf)3 using MW irradiation.
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.
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 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.
How do you Deprotect tert-butyl?
Deprotection of tert-butyl ethers typically involves the use of strong acids (TFA, HBr/AcOH, HCl, etc.) or Lewis acids (Me3SiI, TBDMSOTf, TiCl4, ZnBr2,42 and CeCl3·7H2O/NaI43). Formic acid44is also known to deprotect tert-butyl ethers, but reaction with formic acid is much slower than with aqueous 85 wt % H3PO4.
How do you deprotection tert-butyl ester?
Aqueous phosphoric acid is an effective, environmentally benign, selective and mild reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers are tolerated.
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.
What is Boc2O?
Di-tert-butyl dicarbonate ( Boc2O) is mainly used to introduce a tert-butoxycarbonyl (Boc) protecting group to protect an amino group (especially an amino group of an amino acid), and is one of the commonly used reagents for organic synthesis.