HCID 22121731, compound → 2-[2-fluoro-4-((1S,2S)-2-hydroxycyclo-pentylthio)phenyl]propionic acid
Reaction equation
[O:1]1[C:3]2[CH2:4][CH2:5][CH2:6][C:2]1=2.[F:7][C:8]1[CH:13]=[C:12]([SH:14])[CH:11]=[CH:10][C:9]=1[CH:15]([CH3:20])[C:16]([O:18]C)=[O:17]>ClCCl>[F:7][C:8]1[CH:13]=[C:12]([S:14][C@H:2]2[CH2:6][CH2:5][CH2:4][C@@H:3]2[OH:1])[CH:11]=[CH:10][C:9]=1[CH:15]([CH3:20])[C:16]([OH:18])=[O:17]Participants
4
Procedure
To an aqueous solution (19 mL) of borax (0.1 g, 0.26 mmol), 1,2-epoxycyclopentene (0.8 mL, 9.3 mmol) and compound (9) (1.60 g, 7.5 mmol) were sequentially added. The mixture was stirred at room temperature for 39 hours and dichloromethane (50 mL) was added thereto. The organic layer was washed with water and dried (over sodium sulfate). The solvent was distilled off, and the residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (8:1) solution followed by conventional hydrolysis to give 1.79 g (84%) of compound (16) of interest as yellow oil.