HCID 22121731, compound → 2-[2-fluoro-4-((1S,2S)-2-hydroxycyclo-pentylthio)phenyl]propionic acid

HRID 1506866Notes

Reaction equation

HRID 1506866 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

Reactant 2

HCID 22121731HCID 22121731, compoundHCID 60155350Methyl 2-(2-fluoro-4-mercaptophenyl)propionate

Product 1

HCID 601553552-[2-fluoro-4-((1S,2S)-2-hydroxycyclo-pentylthio)phenyl]propionic acidYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (over sodium sulfate)
  3. distillationThe solvent was distilled off
  4. washthe residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (8:1) solution
  5. customfollowed by conventional hydrolysis

Sources & evidence

ORD record
ord-c551d5d5140741bd810d2a6971460d73
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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