Sodium Hydroxide → Gsk-269984A

HRID 2356613Notes

Reaction equation

HRID 2356613 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>[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

4

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 1

HCID 702EthanolSolvent

Procedure

117 g (0.27 mol) of ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-2-pyridinecarboxylate were dissolved in ethanol (1 litre) (heating required) and 2M sodium hydroxide (200 ml) was added while still hot. Left to crystallise, and when at room temperature was diluted with an equal volume of water. After one hour at room temperature the solid was filtered off and washed with ethanol/water (1:3). MLS (mother liquors) were evaporated to remove ethanol, the solid was filtered off and the two lots were combined and washed with water and ether. Dried in a vacuum oven for 16 hours at 40° C. and 3 days at 60° C. Yield 110.5 g.

Workup

  1. waitLeft
  2. customto crystallise
  3. additionwhen at room temperature was diluted with an equal volume of water
  4. filtrationAfter one hour at room temperature the solid was filtered off
  5. washwashed with ethanol/water (1:3)
  6. customMLS (mother liquors) were evaporated
  7. customto remove ethanol
  8. filtrationthe solid was filtered off
  9. washwashed with water and ether
  10. customDried in a vacuum oven for 16 hours at 40° C. and 3 days at 60° C

Sources & evidence

ORD record
ord-08e2f34df64749dcae11d5a7e9596421
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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