Sodium Hydroxide → 5-(3-tert-Butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylic acid

HRID 534835Notes

Reaction equation

HRID 534835 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[O:13][CH:12]=[N:11][C:10]=1[C:14]([O:16]C)=[O:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[O:13][CH:12]=[N:11][C:10]=1[C:14]([OH:16])=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66750859Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylate

Product 1

HCID 667509145-(3-tert-Butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylic acidYield 32.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylate (Reference Example 21, 6.20 g, 24.3 mmol) and 2 M NaOH (73 mL) in MeOH (290 mL) was stirred at room temperature for 5 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between diethyl ether and water. The water layer was acidified with 1 M HCl and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.92 g) as a light brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between diethyl ether and water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b7b823c2e9d4cfdaca274210a2f9768
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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