The (1-methyl)cyclopropyloxycarbonyl (MPoc) carbamate: a new protecting group for amines

The (1-methyl)cyclopropyl carbamate (MPoc) group represents a new and useful protecting group for amines. It adds relatively little molecular weight and has a simple 1H NMR spectrum. It is orthogonal to the commonly used BOC, Cbz, Alloc, and FMOC groups. MPoc protected amines are resistant to extremes of pH, amines, halogens, many oxidizing agents, and to hydrogenation at ambient temperature. The MPoc group is cleaved by exposure to hypobromous acid or upon hydrogenolysis over palladium at 80 °C.

The (1-methyl)cyclopropyl carbamate (MPoc) group represents a new and useful protecting group for amines. It is orthogonal to the commonly used BOC, Cbz, and FMOC groups. It is cleaved by exposure to hypobromous acid or upon hydrogenolysis over palladium at 80 °C.