Alkyl and aryl-thiotrifluoroacetates and process
US7470810B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jan 11, 2005 |
| Grant date | Dec 30, 2008 |
| Priority date | — |
| Expiry date | Sep 26, 2026 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Novel C3-C19 alkyl- and aryl-thiotrifluoroacetates are provided which have the structurewherein Q is C9-C19 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 C3-C19 alkyl- and aryl-thiotrifluoroacetates is also provided wherein a C3-C19 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 C3-C19 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 C3 to C19 alkyl- or aryl-thiotrifluoroacetate in basic aqueous solution.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.