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Synthesis of Hydrogels with Antifouling Properties As Membranes for Water Purification

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Published on: April 7, 2017

N-Boc deprotection and isolation method for water-soluble zwitterionic compounds.

Zhijian Liu¹, Nobuyoshi Yasuda, Michael Simeone

¹Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.

The Journal of Organic Chemistry

|November 8, 2014

Summary

A new method efficiently removes Boc protecting groups to isolate zwitterionic compounds, including the drug MK-7655 and peptides. A catalytic version was also developed.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Process Chemistry

Background:

N-Boc protected compounds are common synthetic intermediates.
Deprotection and isolation of zwitterionic compounds can be challenging.
Efficient manufacturing processes are crucial for drug development.

Purpose of the Study:

To develop a highly efficient method for deprotecting N-Boc derivatives and isolating zwitterionic compounds.
To demonstrate the applicability of this method in a pharmaceutical manufacturing process.
To explore a catalytic version of the deprotection reaction.

Main Methods:

Tetramethyl-succinimide (TMSI)-mediated deprotection of N-Boc groups.
Direct isolation of zwitterionic products.
Application in the synthesis of the beta-lactamase inhibitor MK-7655.
Testing the method on dipeptides and tripeptides.
Development of a catalytic deprotection using BSA or BSTFA.

Main Results:

Successful deprotection and isolation of various zwitterionic compounds.
Demonstration of the method's utility in the manufacturing of MK-7655.
Expansion of the method's scope to include peptides.
Establishment of a catalytic deprotection protocol.

Conclusions:

The developed TMSI-mediated method offers an efficient route to zwitterionic compounds.
This process is suitable for large-scale synthesis, as shown with MK-7655.
The catalytic approach provides a greener and potentially more cost-effective alternative.