2-Methyl-2-butene → HCID 178454342, compound

HRID 1875072Notes

Reaction equation

HRID 1875072 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][C:29]([CH:33]=[O:34])=[C:30]([Br:32])[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>[CH3:26][C:23]([O:22][C:20]([N:19]([C:17]([O:16][C:13]([CH3:12])([CH3:14])[CH3:15])=[O:18])[C:27]1[NH:28][C:29]([C:33]([OH:5])=[O:34])=[C:30]([Br:32])[N:31]=1)=[O:21])([CH3:24])[CH3:25]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 178454341HCID 178454341, compound

Product 1

HCID 178454342HCID 178454342, compoundYield 30.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium chlorite (0.348 g, 3.84 mmol) and sodium dihydrogenphosphate monohydrate (0.318 g, 2.306 mmol) in water (4 mL) was added to a solution of bis(1,1-dimethylethyl)(4-bromo-5-formyl-1H-imidazol-2-yl)imidodicarbonate (0.150 g, 0.384 mmol), 2-methyl-2-butene (2M in THF) (2.402 mL, 4.80 mmol), t-BuOH (2 mL) and THF (6 mL). The mixture was stirred at RT overnight and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. The residue was triturated with ether to give the desired product (0.047 g, 30%) as a white solid. ES MS: m/z 406 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-03d9090abadb48d7b2f7f5ab1a5cfd75
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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