Synthesis of methyl 2-fluoroacrylate
AssigneeVifor (International) AG
InventorsYongqi Mu, Jessica Brunke
Life of this patent
Estimating the term…
Abstract
Methods for the synthesis of methyl 2-fluoroacrylate (MFA) are provided. The methods include use of various hydrofluorination agents using a variety of starting materials and reaction schemes. The methyl 2-fluoroacrylate prepared by the methods described herein can further be used to prepare patiromer calcium sorbitex.
Claims40
A process for preparing a fluoroacrylate compound of Formula 2A comprising contacting a compound of Formula 5 with an epoxidation agent and a fluorination agent to form the compound of Formula 2A;
- the compound of Formula 5 corresponding to the following structure:
- wherein
- R1 is alkyl or aryl;
- and
- the compound of Formula 2A corresponding to the following structure:
- wherein
- R1 is defined above.
A process for preparing a fluoroacrylate compound of Formula 2A comprising contacting a compound of Formula 6 with a strong base to form a dehydrofluorinated intermediate and reacting the intermediate with an alcohol, R1OH, and a strong acid to form the compound of Formula 2A;
- the compound of Formula 6 corresponding to the following structure:
- wherein
- R1 is alkyl or aryl;
- and
- the compound of Formula 2A corresponding to the following structure:
- wherein
- R1 is defined above.
A process for preparing a fluoroacrylate compound of Formula 2 comprising contacting an alkyl propiolate compound of Formula 1 with a hydrofluorination agent in the presence of a catalyst to form the compound of Formula 2;
- the compound of Formula 1 corresponding to the following structure:
- wherein
- R1 is alkyl or aryl;
- the compound of Formula 2A corresponding to the following structure:
- wherein R1 is defined above,
- provided when the hydrofluorination agent is 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) complex with HF (DMPU-HF), R1 is methyl.
A process for preparing a fluoroacrylate compound of Formula 2 comprising contacting a compound of Formula 4 with a hydrofluorination agent in the presence of a Lewis acid catalyst, a strong base and an alcohol to form the compound of Formula 2;
- the compound of Formula 4 corresponding to the following structure:
- wherein
- R2 is hydrogen, alkyl, or aryl;
- and
- the compound of Formula 2 corresponding to the following structure:
- wherein
- R1 is alkyl or aryl;
- and
- R2 is defined above.
Dependencies are inferred from the claim text.