Sodium Hydroxide → HCID 86604664, compound

HRID 1391815Notes

Reaction equation

HRID 1391815 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:26]=[CH:25][C:24](CCC(OCC)=O)=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-:36].[Na+]>C1COCC1.CO>[F:34][C:2]([F:1])([F:35])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH:13]([CH3:12])[C:15]([OH:20])=[O:36])=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58629833HCID 58629833, compound

Product 1

HCID 86604664HCID 86604664, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-{4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoate (92 mg, 0.19 mmol) in THF (3 mL) and methanol (3 mL) was added, drop-wise, aqueous NaOH (2M, 3 mL). After 17 hours the mixture was concentrated under vacuum and the solid residue acidified with aqueous HCl (2M, 3.5 mL), diluted with water (10 mL) and extracted with DCM (2×10 mL). The combined organic layer was washed with brine (20 mL), dried (MgSO4) and concentrated under vacuum. The acid was loaded onto a PE-AX isolute SPE cartridge (pre-conditioned with 1 column volume of methanol) in 9 mL of methanol and a few drops of Et3N. The cartridge was washed with 3 column volumes of methanol followed by 10% aqueous HCl (2M) in methanol (2×5 mL) and 20% aqueous HCl (2M) in methanol (2×5 mL), yielding the title compound (38 mg).

Workup

  1. concentrationAfter 17 hours the mixture was concentrated under vacuum
  2. additiondiluted with water (10 mL)
  3. extractionextracted with DCM (2×10 mL)
  4. washThe combined organic layer was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. washThe cartridge was washed with 3 column volumes of methanol

Sources & evidence

ORD record
ord-d778386ae16246149280d1d66fe397f8
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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