Alkyl and aryl-thiotrifluoroacetates and process

Details Alkyl and aryl-thiotrifluoroacetates and process Alkyl and aryl-thiotrifluoroacetates and process

2005-01-11

2008-12-30

Wilson, James O. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

Reexamination Certificate

active

07470810

ABSTRACT:
Novel C3-C19alkyl- and aryl-thiotrifluoroacetates are provided which have the structurewherein Q is C9-C19alkyl 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 C3-C19alkyl- and aryl-thiotrifluoroacetates is also provided wherein a C3-C19alkylthiol 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 C3-C19alkyl- 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 C3to C19alkyl- or aryl-thiotrifluoroacetate in basic aqueous solution.

REFERENCES:
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patent: 2005/073185 (2005-11-01), None
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U.S. Appl. No. 60/600,510, filed Aug. 11, 2004, Padam Sharma et al.
U.S. Appl. No. 10/716,012, filed Nov. 18, 2003, Truc Vu et al.

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