2-Methyl-2-butene → HCID 58460141, compound

HRID 536537Notes

Reaction equation

HRID 536537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)=[CH:4][CH:3]=1.CC(=CC)C.Cl([O-])=[O:34].[Na+]>CC(C)=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([OH:34])=[O:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 58460129HCID 58460129, compound

Product 1

HCID 58460141HCID 58460141, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

An amount of 345 mg (0.73 mmol) of the compound from Example 14A and also 0.58 ml (5.45 mmol) of 2-methyl-2-butene were dissolved in 3 ml of acetone and admixed at RT with a solution of 376 mg (2.73 mmol) of sodium dihydrogenphosphate-1-hydrate and 460 mg (4.07 mmol) of sodium chlorite in 9 ml of water. The mixture was stirred at this temperature for 16 hours thereafter and then diluted with 15 ml of water and with 15 ml of ethyl acetate. After the phases had been separated, the aqueous phase was further extracted with 15 ml of ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulphate. Following filtration, the solvent was concentrated and the residue was dried in a high vacuum. This gave 337 mg (104% of theory) of the target compound, which was reacted further without additional purification.

Workup

  1. customAfter the phases had been separated
  2. extractionthe aqueous phase was further extracted with 15 ml of ethyl acetate
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltration
  6. concentrationthe solvent was concentrated
  7. customthe residue was dried in a high vacuum
  8. customThis gave 337 mg (104% of theory) of the target compound, which was reacted further without additional purification

Sources & evidence

ORD record
ord-08074fdc9fb2466c80f4f108e4b54fa1
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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