Water → (2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)methyl methanesulfonate

HRID 1049613Notes

Reaction equation

HRID 1049613 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:17][C:16]=1[CH2:31][OH:32].O>C1COCC1>[CH3:1][S:2]([O:32][CH2:31][C:16]1[CH:17]=[C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:19]=[CH:20][C:15]=1[C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[F:6])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 117759932(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)methanol

Product 1

HCID 117759799(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.164 mL) was added to a solution of (2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)methanol (390 mg) in THF (10 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give (2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)methyl methanesulfonate. To solution (10 mL) of the obtained compound and TBAI (117 mg) in DMF was added sodium hydride (60%, 85 mg) at 0° C., and the mixture was stirred at 0° C. for 5 min, then at 80° C. for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (326 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f9a66cf8117c4d33a4add1e6556ee3f8
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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