Hydrochloric Acid → HCID 59145196, compound

HRID 2389377Notes

Reaction equation

HRID 2389377 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:30])[N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[O:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:30])[N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[O:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59145284HCID 59145284, compound

Product 1

HCID 59145196HCID 59145196, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)propanoate (155 mg) in MeOH (2.0 mL) was added 1M NaOH aqueous solution (0.482 mL) at ambient temperature and the mixture was stirred at ambient temperature for overnight. The mixture was acidified to pH=3 with 1M HCl aqueous solution and extracted with chloroform (4.0 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:MeOH=9:1) to afford 3-(3-{3-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]propyl}phenoxy)propanoic acid (27.8 mg) as white crystals.

Workup

  1. extractionextracted with chloroform (4.0 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (chloroform:MeOH=9:1)

Sources & evidence

ORD record
ord-33fd745091224b85b2cea1d0dd628599
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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