Pyridine → 2-(3,5-Bis-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pentanoic acid methyl ester

HRID 426356Notes

Reaction equation

HRID 426356 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18](=[O:32])[CH:19]([C:24]1[CH:29]=[C:28]([OH:30])[CH:27]=[C:26](O)[CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22].N1C=CC=CC=1>C(Cl)Cl>[CH3:16][O:17][C:18](=[O:32])[CH:19]([C:24]1[CH:29]=[C:28]([O:30][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:8])=[O:6])[CH:27]=[C:26]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 590047662-(3,5-Dihydroxy-phenyl)-4-methyl-pentanoic acid methyl ester

Product 1

HCID 590047892-(3,5-Bis-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pentanoic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (208 μL, 1.26 mmol) was added dropwise to a stirred solution of 2-(3,5-dihydroxy-phenyl)-4-methyl-pentanoic acid methyl ester (50 mg, 0.21 mmol) and pyridine (195 μL, 2.52 mmol) in DCM (5 mL) at 0° C. then warmed to room temperature. After 1 h, the mixture washed with 1M HCl (2 mL), dried (MgSO4) and concentrated in vacuo to afford the title product as an orange oil (104 mg, 99%). The product was used without further purification in the next step

Workup

  1. washthe mixture washed with 1M HCl (2 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6e0258e68c945baacc58a9238da8512
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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