2-Methyl-2-butene → HCID 70937195, compound

HRID 1875261Notes

Reaction equation

HRID 1875261 reaction equation
[O-:1]Cl=O.[Na+].[Cl:5][C:6]1[N:7]=[C:8]([S:21]([NH:24][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]([NH:24][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 86761670HCID 86761670, compound

Product 1

HCID 70937195HCID 70937195, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of NaClO2 (0.21 g, 2.34 mmol) and NaH2PO4.H2O (0.19 g, 1.41 mmol) in H2O (0.5 mL) was added to a solution of 4-chloro-5-formyl-N-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonamide (0.083 g, 0.23 mmol) and 2-methyl-2-butene (1.41 mL of a 2M solution in THF, 2.81 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-[(methylamino)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-6b4628c0274a4c96a65c0034fe51aa07
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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