Acetic Acid → Gsk-269984B

HRID 2356614Notes

Reaction equation

HRID 2356614 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O-:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[Na+].O.C(O)(=O)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 23696973Gsk-269984A

Product 1

HCID 11495634Gsk-269984B

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-2-pyridinecarboxylate (3.0 g) was suspended in ethyl acetate (100 ml) and water (100 ml) with stirring. Acetic acid (1.0 ml) was added to give two clear phases which were separated. The ethyl acetate layer was dried over magnesium sulfate and concentrated to give an oil which crystallised after a few minutes. Toluene (100 ml) was added and the solution was re-evaporated to give a white solid. Left at 20 mBar for 5 hours at 45° C. 2.69 g.

Workup

  1. customto give two clear phases which
  2. customwere separated
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil which
  6. customcrystallised after a few minutes
  7. additionToluene (100 ml) was added
  8. customthe solution was re-evaporated
  9. customto give a white solid

Sources & evidence

ORD record
ord-2ab341abf424456fa9e9a31cb968789a
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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