Sodium Bicarbonate → [1-(5-Formyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester

HRID 381522Notes

Reaction equation

HRID 381522 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]([C:16]1[CH:20]=[C:19]([CH:21](OCC)[O:22]CC)[O:18][N:17]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>OS(O)(=O)=O.CC(C)=O>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]([C:16]1[CH:20]=[C:19]([CH:21]=[O:22])[O:18][N:17]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 18682348[1-(5-Diethoxymethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester

Product 1

HCID 18682349[1-(5-Formyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl esterYield 53.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 180AcetoneSolvent

Procedure

A stirred mixture of [1-(5-diethoxymethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester (920 mg, 2.4 mmol), acetone (50 ml) and H2SO4 (10 drops) was heated to reflux. After 35 min. the mixture was cooled to room temperature, neutralized with solid NaHCO3 and concentrated under reduced pressure. The resulting paste was taken up in EtOAc; washed with water and brine; dried over Na2SO4; filtered; and concentrated under reduced pressure to give a light yellow oil. Purification by Flash 40(small) chromatography eluting with 1:3 EtOAc/hexane gave 407 mg of the title compound as a light yellow oil. MS [M+1]+ 317.

Workup

  1. temperaturewas heated to reflux
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationand concentrated under reduced pressure
  7. customto give a light yellow oil
  8. customPurification by Flash 40(small) chromatography
  9. washeluting with 1:3 EtOAc/hexane

Sources & evidence

ORD record
ord-48230612f58c427e8a36043bbaa45c7a
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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