DCC mediated coupling for halofenate manufacture
AssigneeCymaBay Therapeutics, Inc.
InventorJiangao Song
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Abstract
The present application discloses a process for the preparation of a halofenate compound of the formula (III) or a salt thereof: wherein R, X and X′ are as defined herein, the process comprising contacting a compound of formula (Ia) with a compound of formula (Ib) and N,N′-dicyclohexylcarbodiimide under conditions sufficient to form the compound of formula (III).
Claims20
A process for preparing a compound of formula (IV)
- where R is C1-6alkylC(O)NHC1-6alkyl or arylC(O)NHC1-6alkyl, comprising the step of contacting (−)-halofenic acid with a compound of the formula ROH and N,N′-dicyclohexylcarbodiimide in an aprotic solvent in the absence of base under conditions sufficient to form the compound of formula (IV).
A process for the preparation of (−)-halofenate, comprising the step of contacting (−)-halofenic acid with N-acetylethanolamine and N,N′-dicyclohexylcarbodiimide in an aprotic solvent in the absence of base under conditions sufficient to form the (−)-halofenate.
A process for the preparation of (−)-halofenate, comprising the steps of:
- contacting a solution comprising N-acetylethanolamine in toluene free of base with a solution comprising (−)-halofenic acid in toluene free of base;
- cooling the resulting solution at about 0° C.;
- contacting a solution of N,N′-dicyclohexylcarbodiimide in toluene free of base with the cooled resulting solution for a sufficient period of time to form (−)-halofenate.
Dependencies are inferred from the claim text.