[Cl:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:5]=[C:6]([Cl:17])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][C@@H:12](CO)[O:11][C:10]1=[O:16].[OH-].[Na+].I(O)(=O)(=O)=[O:28].Cl>C1COCC1.O.CCOC(C)=O>[Cl:17][C:6]1[CH:5]=[C:4]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH:12]([OH:28])[O:11][C:10]1=[O:16]
To (3R,5S)-3-(3,5-dichloro-4′-fluoro-biphenyl-4-ylmethyl)-5-hydroxymethyl-dihydro-furan-2-one (375 g, 1.015 mmoles) dissolved in 5 vols of THF, add 750 mL of 2 N NaOH. After 40 min, add periodic acid (375 g, 1,644 mmoles), dissolved in 1,125 mL of water, over 17 min (Tmax 33° C.). Add EtOAc (3 L) followed by 800 mL of 5.0 N HCl and 600 mL of water. Agitate the layers and then separate. Wash the organic layer with 100 g of sodium thiosulfate in 1 L of water, then 1 L of water, and then 700 mL of saturated NaCl in water. Dry the organic layer over sodium sulfate and then solvent exchange into 4 volumes (1500 mL) of heptane. Collect the solid by filtration and dry under vacuum. Reslurry the resulting solid in 3 volumes (1 L) of acetonitrile at 55° C. Cool the mixture in an ice bath and collect the solid by filtration. Dry the solid under vacuum to afford 273 g (78% yield) of the title compound as a white solid. MS (m/z): 355 (M+1, 35Cl), 357 (M+1, 37Cl).
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