Novel C.sub.3-C.sub.19 alkyl- and aryl-thiotrifluoroacetates are provided
which have the structure 1
wherein Q is C.sub.9-C.sub.19 alkyl or aryl, and are useful protecting
agents for the amino or hydroxy functional groups of amines, amino acids
or primary or secondary alcohols or amino alcohols to enable formation of
amide bonds in peptides or proteins which are useful as screening agents,
pharmaceuticals and cosmetics.
A process for preparing C.sub.3-C.sub.19 alkyl- and
aryl-thiotrifluoroacetates is also provided wherein a C.sub.3-C.sub.19
alkylthiol or arylthiol is treated with trifluoroacetic anhydride (TFAA)
in the presence of organic base such as pyridine, a solvent such as
dichloromethane (DCM) and dimethylaminopyridine (DMAP) as a catalyst to
form the desired C.sub.3-C.sub.19 alkyl- or aryl-thiotrifluoroacetate.
In addition, a process for protecting a primary or secondary amino group
or a primary or secondary hydroxyl group or an amino alcohol with a
trifluoroacetyl protecting group is provided wherein a primary or
secondary amine, amino acid, a primary or secondary alcohol or an amino
alcohol is treated with a C.sub.3 to C.sub.19 alkyl- or
aryl-thiotrifluoroacetate in basic aqueous solution.
