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A Facile Method for the Preparation of MOM-Protected Carbamates

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journal contribution
posted on 2009-01-15, 00:00 authored by David M. Barnes, Jufang Barkalow, Daniel J. Plata
A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched with methanol to afford MOM-protected carbamates. The process is tolerant of a variety of functionalities, including Boc, sulfonamide, and acetamide protecting groups. Mild conditions for the removal of the MOM group are also described; selective deprotection of the MOM group in the presence of a Boc group has been demonstrated.

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