2-Methyl-2-butene → HCID 70937207, compound

HRID 1875255Notes

Reaction equation

HRID 1875255 reaction equation
[O-:1]Cl=O.[Na+].[Cl:5][C:6]1[N:7]=[C:8]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:10]=1[CH:11]=[O:12].CC(=CC)C>O.C1COCC1.CC(O)(C)C>[Cl:5][C:6]1[N:7]=[C:8]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:18])[CH3:19])[C:10]=1[C:11]([OH:1])=[O:12]

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86761668HCID 86761668, compound

Product 1

HCID 70937207HCID 70937207, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of NaClO2 (0.21 g, 2.31 mmol) and NaH2PO4.H2O (0.19 g, 1.39 mmol) in H2O (0.5 mL) was added to a solution of 4-chloro-5-formyl-N,N-dimethyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonamide (0.085 g, 0.23 mmol) and 2-methyl-2-butene (1.39 mL of a 2M solution in THF, 2.77 mmol) in THF (0.70 mL) and t-BuOH (0.16 mL). The reaction mixture was stirred at RT for 1 h and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and dried to provide 4-chloro-2-[(dimethylamino)sulfonyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid as a clear oil that was assumed to be quantitative and used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-6ec3a6a10d294cdf88cd7e96a3a8b9f5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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