Sodium Hydroxide → 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylic acid

HRID 1957582Notes

Reaction equation

HRID 1957582 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:23]=[C:22]([C:24]([O:26]C)=[O:25])[O:21][N:20]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[O:21][N:20]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19068162Methyl 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylate

Product 1

HCID 190681503-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-4 (2.7 g, 6.9 mmol), CH3OH (50 mL), and 1N NaOH (13.9 mL, 13.9 mmol) was stirred at ambient temperature for 1 h. The CH3OH was evaporated and the resulting aqueous portion acidified with 1M NaHSO4. The solution was extracted with EtOAc (3×) and then the extracts were combined, dried (MgSO4), and concentrated to give 4-5 (2.5 g) as a solid.

Workup

  1. customThe CH3OH was evaporated
  2. extractionThe solution was extracted with EtOAc (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-88b2790005fc43e0bd7cb5b799f4e7bd
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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