Hydrochloric Acid → HCID 57443475, compound

HRID 546815Notes

Reaction equation

HRID 546815 reaction equation
Cl.C([Si]([O:9][CH:10]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH2:42][CH3:43])([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[O:33][C:34]([CH:37]=[CH:38][O:39]C)=[CH:35][CH:36]=3)=[C:28]([CH3:41])[CH:27]=2)[CH2:24][CH3:25])=[CH:19][C:18]=1[CH3:44])[C:11]([CH3:14])([CH3:13])[CH3:12])(C)C)(C)(C)C.C(=O)(O)[O-:46].[Na+].P([O-])(O)(O)=O.[Na+].Cl[O-].[Na+].CC(=CC)C.S(=O)(=O)(O)[O-].[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:42]([C:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][C:34]([CH2:37][C:38]([OH:46])=[O:39])=[CH:35][CH:36]=2)=[C:28]([CH3:41])[CH:27]=1)([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][CH:10]([OH:9])[C:11]([CH3:13])([CH3:12])[CH3:14])=[C:18]([CH3:44])[CH:19]=1)[CH2:24][CH3:25])[CH3:43]

Participants

10

Reactant 7

HCID 313Hydrochloric Acid2×HCID 105532-Methyl-2-buteneHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphateHCID 67065031HCID 67065031, compound

Product 1

HCID 57443475HCID 57443475, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
65 °C

Procedure

2 N Hydrochloric acid aqueous solution (0.2 mL) was added to a solution of t-butyl-(1-{2-[4-(1-ethyl-1-{4-[5-(2-methoxy-vinyl)-furan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)-dimethyl-silane (Example 4-(1); 20 mg, 0.033 mmol) in tetrahydrofuran (0.5 mL) at room temperature, and the mixture was stirred at 65° C. for two hours. Tetrahydrofuran (0.3 mL) and 4 N hydrochloric acid aqueous solution (0.2 mL) were further added to the mixture at room temperature, and the mixture was stirred at 65° C. for two hours. A saturated aqueous sodium bicarbonate solution and ethyl acetate were added to the reaction mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=3/1). The resulting product (6 mg) was dissolved in water (0.1 mL) and t-butanol (0.4 mL). Sodium dihydrogenphosphate (2.9 mg, 0.019 mmol), sodium hypochlorite (3.4 mg, 0.038 mmol) and 2-methyl-2-butene (0.013 mL, 0.126 mmol) were added at room temperature, and the mixture was stirred at the same temperature for one hour. A saturated aqueous potassium bisulfate aqueous solution and ethyl acetate were added to the reaction mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=2/1) to give the title compound (1.2 mg, 7%).

Workup

  1. stirringthe mixture was stirred at 65° C. for two hours
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (hexane/ethyl acetate=3/1)
  6. dissolutionThe resulting product (6 mg) was dissolved in water (0.1 mL)
  7. stirringthe mixture was stirred at the same temperature for one hour
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by preparative TLC (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-8153e90c3834443f983e7bd3bce7b741
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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