Potassium Carbonate → Isohexane ethyl acetate

HRID 1677879Notes

Reaction equation

HRID 1677879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]2[C:19]([OH:25])=[CH:20][CH:21]=[C:22]([F:24])[CH:23]=2)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])(=[O:10])=[O:9].CC1C=CC(S([O:36][C@H:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:7][CH2:2][CH2:3][CH:4]([CH3:18])[CH3:5].[C:37]([O:25][CH2:19][CH3:20])(=[O:36])[CH3:38].[F:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[O:25][C@@H:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39])[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 12884153(R)-2-Tosyloxypropionic acid methyl esterHCID 672415383',5-Difluoro-4'-[(2-fluorophenyl)sulfonyl]biphenyl-2-ol

Product 2

HCID 21882781Isohexane ethyl acetateHCID 67240103Methyl (2s)-2-({3',5-difluoro-4'-[(2-fluorophenyl)sulfonyl]biphenyl-2-yl}oxy)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The product of step (v) (175 mg), the product of step (vi) (124 mg) and potassium carbonate (133 mg) in acetonitrile (10 ml) were charged to a flask and stirred at 65° C. overnight. The reaction mixture was cooled, diluted with water (20 ml) and extracted with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane then 4:1 isohexane/ethyl acetate to give the sub-title compound as a colourless oil, yield 121 mg.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with isohexane

Sources & evidence

ORD record
ord-00c800cf13864507bdb9681f9f72b22d
Source dataset
uspto-grants-2011_08
Patent number
US08008350B2

Reaction notes

Loading…