A facile method for the preparation of MOM-protected carbamates.
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.
Barnes
David M
DM
GPRD Process Research and Development, Abbott Laboratories, Building R13/3, 1401 Sheridan Road, North Chicago, Illinois 60064, USA. david.barnes@abbott.com
Barkalow
Jufang
J
Plata
Daniel J
DJ
D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008737:Methyl Chloride / Q000737:chemistry; D008745:Methylation
D002219:Carbamates; D008737:Methyl Chloride