Asymmetric process for preparing florfenicol, thiamphenicol,...

C - Chemistry – Metallurgy – 07 – C

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C07C 317/32 (2006.01) C07C 231/10 (2006.01) C07C 233/18 (2006.01) C07C 315/04 (2006.01) C07D 263/14 (2006.01)

Patent

CA 2152089

The present invention comprises a process for the asymmetric synthesis of florfenicol, thiamphenicol or chloramphenicol. In an alternative embodiment, the present invention comprises a process for isomerizing of the S,S-isomer of florfenicol to the R,S-isomer (I)] by sequentially treating with: (i) a lower alkylsulfonyl chloride and a tertiary amine base; (ii) sulfuric acid and water, (iii) an alkali metal hydroxide. The present invention further comprises a process for regioselectively opening an epoxide to form a threo-oxazoline.

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