Sodium Hydroxide → 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acid

HRID 1026207Notes

Reaction equation

HRID 1026207 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH3:23])[CH2:12][O:13][C:14]1[CH:18]=[C:17]([C:19]([O:21]C)=[O:20])[O:16][N:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CO>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH3:23])[CH2:12][O:13][C:14]1[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[O:16][N:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67778409methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylate

Product 1

HCID 677777153-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2M Aqueous sodium hydroxide solution (20 mL) was added to a solution of methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylate (4.0 g) in THF/methanol (20 mL/20 mL), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated under reduced pressure, and the residue was neutralized with 6M hydrochloric acid and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.5 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0002d7f6ad81411db0fb432c3da4a95d
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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