Trifluoroacetic acid → HCID 86686247, compound

HRID 1021303Notes

Reaction equation

HRID 1021303 reaction equation
C([O:5][C:6]1[N:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:16][N:15]([C:17]3[C:18]([F:25])=[C:19]([CH2:23][OH:24])[CH:20]=[CH:21][CH:22]=3)[CH2:14]2)=[CH:8][CH:7]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:25][C:18]1[C:19]([CH2:23][OH:24])=[CH:20][CH:21]=[CH:22][C:17]=1[N:15]1[CH2:14][CH:13]([O:12][C:9]2[CH:8]=[CH:7][C:6](=[O:5])[NH:11][CH:10]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68310271HCID 68310271, compound

Product 1

HCID 86686247HCID 86686247, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-{3-[(6-tert-Butoxypyridin-3-yl)oxy]azetidin-1-yl}-2-fluorophenyl)methanol (760 mg) was mixed with dichloromethane (5 ml), and TFA (2 ml) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and a 1 M aqueous NaOH solution and CHCl3 were added thereto. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 5-({1-[2-fluoro-3-(hydroxymethyl)phenyl]azetidin-3-yl}oxy)pyridin-2(1H)-one (428 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 1 M aqueous NaOH solution and CHCl3 were added
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-852747af29b44880872657443683eb79
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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