Sodium Hydroxide → HCID 58370204, compound

HRID 2062085Notes

Reaction equation

HRID 2062085 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]([C:31](=[O:33])[CH3:32])[CH2:27][CH2:26]1)=[O:11])([CH3:8])[CH2:6][CH3:7])C.[OH-].[Na+]>C1COCC1.CO>[C:31]([N:28]1[CH2:27][CH2:26][CH:25]([CH2:24][O:23][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]([Cl:22])=[CH:21][C:12]=2[C:10]([NH:9][C:5]([CH3:8])([CH2:6][CH3:7])[C:4]([OH:34])=[O:3])=[O:11])[CH2:30][CH2:29]1)(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66701094HCID 66701094, compound

Product 1

HCID 58370204HCID 58370204, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 70 mg of 2-{[1-(1-acetyl-piperidin-4-ylmethoxy)-4-chloro-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester in 4 mL THF and 1 mL MeOH was treated with 4 mL of 2 M aqueous sodium hydroxide. The reaction mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo. The residue was taken up in 6 mL of water and washed with ethyl acetate. The aqueous phase was treated with 2 M hydrochloric acid to pH 4, then extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated to give 30 mg of 2-{[1-(1-acetyl-piperidin-4-yl-methoxy)-4-chloro-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid.

Workup

  1. customThe organic solvent was removed in vacuo
  2. washwashed with ethyl acetate
  3. additionThe aqueous phase was treated with 2 M hydrochloric acid to pH 4
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a5d894d66c88450bb2fe3a51726c5b02
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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