Sodium Hydroxide → 4-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

HRID 2289342Notes

Reaction equation

HRID 2289342 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[O:24][CH3:25].[OH-].[Na+]>CCO>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][CH:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[C:5]([O:24][CH3:25])[CH:6]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10570851Tert-butyl 4-(3-methoxy-4-(methoxycarbonyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 105458744-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-methoxybenzoic acid methyl ester (1.0 g, 2.7 mmol) from Step 2 was refluxed in EtOH (15 mL) containing aqueous NaOH (5.5 mL of a 1.0 N solution). The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (50 mL). The organic phase was washed with water (25 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-t-Butoxycarbonyl-4-piperidinyloxy)-2-methoxy-benzoic acid as an amorphous solid.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (50 mL)
  3. washThe organic phase was washed with water (25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c3cb91e6ac664d0e95b22ef86200b837
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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