Question

Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

Short answer

Reaction mechanism constitutes a step-by-step explanation of what happens in a particular reaction. The elementary process comprises the term used to indicate each specific reaction step.

Step-by-step solution

Reaction mechanism

Reaction mechanism constitutes a step-by-step explanation of what happens in a particular reaction. The elementary process comprises the term used to indicate each specific reaction step.

F moc group

F moc group constitutes an amino protecting group, which comprises 9-fluorenylmethoxycarbonyl and is created by combining amino acid with 9-fluorenylmethyl chloroformate. The F moc group can be removed using a base like ${\mathbf{NH}}_{\mathbf{3}}$ or an amine.

Mechanism for the reaction that removes a Fmoc group from an amino acid

The piperidine abstracts an acidic proton from the starting material.This generates a negative charge on the carbon atom. The conjugation of the negative charge eliminates the carbon dioxide in the next step.

The protonation of the amino group follows this. The final step involves the proton transfer from the acid to an imine leading to the final product. The mechanism can be given as: