Sodium Hydroxide → 3-Tert-butylaminocarbonyl-5-methylisoxazole-4-carboxylic acid

HRID 1590007Notes

Reaction equation

HRID 1590007 reaction equation
[OH-].[Na+].[C:3]([NH:7][C:8]([C:10]1[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([CH3:20])[O:12][N:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.C(O)C>[C:3]([NH:7][C:8]([C:10]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:20])[O:12][N:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 156825714-Ethoxycarbonyl-5-methyl-isoxazole-3-carboxylic acid-tert-butylamide

Product 1

HCID 105134073-Tert-butylaminocarbonyl-5-methylisoxazole-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

At from 5° to 10° C. and under a nitrogen blanket, 1.0 g (25.0 mmol) of sodium hydroxide in 50 ml of water was dripped into a solution of 5.4 g (21.3 mmol) of 4-ethoxycarbonyl-5-methyl-isoxazole-3-carboxylic acid-tert-butylamide in 100 ml of ethanol, and the mixture was stirred for 12 hours at room temperature. The solution was evaporated down, the residue was taken up in 150 ml of water, the pH was adjusted to 8-9, and the mixture was extracted twice, each time with 100 ml of diethylether. The aqueous phase was then acidified to a pH of 2 with 6N HCl, followed by extraction four times, each time with 200 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate and the solvent was stripped off under reduced pressure. Yield: 95%; yellow solid.

Workup

  1. customAt from 5° to 10° C.
  2. customThe solution was evaporated down
  3. extractionthe mixture was extracted twice
  4. extractionfollowed by extraction four times
  5. dry with materialThe combined organic phases were dried over magnesium sulfate

Sources & evidence

ORD record
ord-50c29ef7bc184747b2905be09b33b084
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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