2-Methyl-2-butene → 3-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic Acid

HRID 83578

Reaction equation

HRID 83578 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[CH:10]2[C:8]([CH:13]=[O:14])([CH2:9]2)[CH2:7]1.O.O.P([O-])(O)(O)=[O:24].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O1CCCC1.O.O>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[CH:10]2[C:8]([C:13]([OH:24])=[O:14])([CH2:9]2)[CH2:7]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 866803893-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carbaldehyde

Product 1

HCID 866803903-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic AcidYield 32.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22124471t-Butanol tetrahydrofuran waterSolvent

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere, to a solution of 3-(2,4-dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carbaldehyde (10.8 mg) in tert-butanol/tetrahydrofuran/water (4/3/1, 0.5 ml) was added sodium dihydrogenphosphate dihydrate (20.2 mg) at room temperature. This reaction mixture was cooled to 0° C., 2-methyl-2-butene (18 μl) and sodium chlorite (9.0 mg) were sequentially added thereto, and then the mixture was stirred at room temperature for 24 hours. This reaction mixture was cooled to 0° C., and then water was added thereto, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1) to give the titled compound (3.7 mg).

Workup

  1. temperatureThis reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-0c337cdeb8dc458b94b46fd9137580fc
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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