4-Toluenesulfonyl chloride → HCID 11338856, compound

Participants

Reaction Steps

A solution of crude (2R,3S or 2S,3R)-2-[(S)-(4-chlorophenyl)(cyclopropyl)methyl]-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-3-hydroxybutanoic acid (Diastereomer E) (0.72 g, 1.5 mmol), tosyl chloride (0.58 g, 3.0 mmol) and collidine (20 ml) is heated at 170° C. for 2 hours. The mixture is concentrated in vacuo and the residue chromatographed on silica gel eluting with ether:hexane (5:95) to yield the title compound as a colorless liquid (0.43 g, 69% from diasteriomer B), [α]D=+35.8 (C=0.0438, CHCl3) which is characterized by 1HNMR and 19FNMR spectral analyses.

Provenance & Evidence