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Acetyl Protection








Common Conditions (Protection):


Acetyl Chloride

Acetyl protection of amines can be easily carried out with acetyl chloride (AcCl) in the presence of a base (ex. TEA or DIEA) with an appropriate solvent (ex. THF or DCM).[1]






Common Conditions (Deprotection):


Basic Conditions

Acetamides can be deprotected in the presence of a hydroxide base (ex. KOH or NaOH) in an appropriate solvent (ex. EtOH/H2O) at elevated temperatures (ex. reflux) . These harsh conditions may not be compatible with base sensitive substrates.





Acidic Conditions

Acetamides can be deprotected in the presence of a strong acid (ex. HCl) in an appropriate solvent (ex. EtOH/H2O) at elevated temperatures (ex. reflux). These harsh conditions may not be compatible with acid sensitive substrates.[1]






References:


1) Wuts, P. G. M.; Greene, T. W.; Greene's Protective Groups in Organic Synthesis, 4th Edition