Sodium Hydroxide → Gsk-269984A

HRID 2356620Notes

Reaction equation

HRID 2356620 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[F:29])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[OH-].[Na+:31]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[F:29])=[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+:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59384237Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

Product 1

HCID 23696973Gsk-269984A

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-2-pyridinecarboxylate (108 mg, 0.25 mmol) was dissolved in 3 ml of ethanol and 1 ml of water. Sodium hydroxide (4 equivalents) was added. The mixture was stirred at 60° C. until TLC showed no more SM (starting material) (˜2 hours). The reaction mixture was cooled down and extracted with ethyl acetate (3×). Dried over MgSO4. Sodium 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}-phenyl)methyl]-2-pyridinecarboxylate was obtained as a white solid (94 mg).

Workup

  1. customno more SM (starting material) (˜2 hours)
  2. temperatureThe reaction mixture was cooled down
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialDried over MgSO4

Sources & evidence

ORD record
ord-901131602ba84feb893401a17e45b533
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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