Trifluoroacetic acid → HCID 86686247, compound

HRID 2171703Notes

Reaction equation

HRID 2171703 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 1M 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 1M 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-e35ded0a67594ea09fc5891707367199
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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