Sodium Hydroxide → HCID 58370216, compound

HRID 2062089Notes

Reaction equation

HRID 2062089 reaction equation
C([O:3][C:4](=[O:34])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]1)=[O:11])([CH3:8])[CH2:6][CH3:7])C.[OH-].[Na+]>C1COCC1.CO>[Cl:22][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([CH:31]([CH3:32])[CH3:33])[CH2:27][CH2:26]2)=[C:12]([C:10]([NH:9][C:5]([CH3:8])([CH2:6][CH3:7])[C:4]([OH:34])=[O:3])=[O:11])[CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66701241HCID 66701241, compound

Product 1

HCID 58370216HCID 58370216, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 36 mg of 2-{[4-chloro-1-(1-isopropyl-piperidin-4-ylmethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester in 3 mL THF and 1 ml MeOH was treated with 3 mL of 2 M aqueous sodium hydroxide. The reaction mixture was stirred at room temperature for 40 hours. The organic solvent was removed in vacuo. The residue was taken up in 6 ml of water, treated with 2 M hydrochloric acid to adjust the pH to 6˜7, then extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated to give 32 mg of 2-{[4-Chloro-1-(1-isopropyl-piperidin-4-ylmethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid.

Workup

  1. customThe organic solvent was removed in vacuo
  2. additiontreated with 2 M hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb4426e234d045ae8eee248e5fd098bd
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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