2-Methyl-2-butene → HCID 178454351, compound

HRID 1875077Notes

Reaction equation

HRID 1875077 reaction equation
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[CH3:12][C:13]([O:16][C:17]([N:19]([C:27]1[NH:28][CH:29]=[C:30]([CH:32]=[O:33])[N:31]=1)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:18])([CH3:15])[CH3:14].CC(=CC)C>O.C1COCC1.CC(O)(C)C>[CH3:15][C:13]([O:16][C:17]([N:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C:27]1[NH:28][CH:29]=[C:30]([C:32]([OH:5])=[O:33])[N:31]=1)=[O:18])([CH3:12])[CH3:14]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 178454349HCID 178454349, compound

Product 1

HCID 178454351HCID 178454351, compoundYield 53.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium chlorite (0.505 g, 5.59 mmol) and sodium dihydrogenphosphate monohydrate (0.463 g, 3.35 mmol) in water (4 mL) was added to a solution of bis(1,1-dimethylethyl)(4-formyl-1H-imidazol-2-yl)imidodicarbonate (0.174 g, 0.559 mmol), 2-methyl-2-butene (2M in THF) (3.49 mL, 6.99 mmol), t-BuOH (2 mL) and THF (6 mL). The mixture was stirred at RT overnight. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated. The residue was triturated with ether and the resulting white solid was dried under vacuum to give 0.098 g (53%) of the title compound. MS m/z 326 (M−1).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was triturated with ether
  5. customthe resulting white solid was dried under vacuum

Sources & evidence

ORD record
ord-aad38660bad042f0a60e49009d4d24f6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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