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 I 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.
Why is deprotection needed?
Protecting groups are needed to temporarily block a certain reactive site on a molecule. The protective group is then chemically removed (deprotected) in a later step and that particular reactive functional group is regenerated.
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.
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.
Can deprotection be PMB?
–p-Methoxybenzyl (PMB or MPM) group can be protected or deprotected under the same conditions as benzyl group. It can also be deprotected under mildly oxidizing conditions using DDQ (dichlorodicyanobenzoquinone) or strongly acidic conditions.
How do you convert ketones to alcohol?
Reduction of other aldehydes gives primary alcohols. Reduction of ketones gives secondary alcohols. The acidic work-up converts an intermediate metal alkoxide salt into the desired alcohol via a simple acid base reaction.
How do you make dioxolane?
Dioxolanes can be prepared by acetalization of aldehydes and ketalization of ketones with ethylene glycol.
How do I get rid of TFA?
How is the deprotection of tert butoxycarbonyl ( Boc ) achieved?
Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 m) in anhydrous dioxane solution for 30 min at room temperature.
When to use nabarf 4 for dioxolane deprotection?
NaBArF 4 can also be used for deprotection of acetal or ketal-protected carbonyl compounds. For example, deprotection of 2-phenyl-1,3-dioxolane to benzaldehyde can be achieved in water in five minutes at 30 °C.
How is the ring of dioxolane prepared?
Dioxolanes are a group of organic compounds containing the dioxolane ring. Dioxolanes can be prepared by acetalization of aldehydes and ketalization of ketones with ethylene glycol. (+)-cis-Dioxolane is the trivial name for L-(+)-cis-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is a muscarinic acetylcholine receptor agonist.
Which is used to convert neosporol to dioxolane?
In the case of neosporol, a Prilezhaev reaction with trifluoroperacetic acid is used to convert a suitable allyl alcohol precursor to an epoxide, which then undergoes a ring-expansion reaction with a proximate carbonyl functional group to form the dioxolane ring.
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