Acetonitrile → HCID 118035475, compound

HRID 1775765Notes

Reaction equation

HRID 1775765 reaction equation
[C:1]([O:5][C:6](/[C:8](=[CH:35]\[C:36](\[CH3:51])=[CH:37]\[CH:38]([CH3:50])[CH2:39][CH:40]([CH3:49])[CH2:41][CH:42]([CH3:48])[CH2:43][CH:44]([CH3:47])[CH2:45][CH3:46])/[CH2:9][CH:10]([CH3:34])[C:11]([O:13]C1C(=O)OC(C(OC(C)(C)C)=O)C1C(OC(C)(C)C)=O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(#N)C.[OH-].[Na+]>O>[C:1]([O:5][C:6](/[C:8](=[CH:35]\[C:36](\[CH3:51])=[CH:37]\[CH:38]([CH3:50])[CH2:39][CH:40]([CH3:49])[CH2:41][CH:42]([CH3:48])[CH2:43][CH:44]([CH3:47])[CH2:45][CH3:46])/[CH2:9][CH:10]([CH3:34])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 118035625HCID 118035625, compound

Product 1

HCID 118035475HCID 118035475, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 2) To di-tert-butyl 4-{(4Z,6E)-4-(tert-butoxycarbonyl)-2,6,8,10,12,14-hexamethylhexadec-4,6-dienoyloxy}-5-oxotetrahydrofuran-2,3-dicarboxylate (500 mg, 0.694 mmol) obtained in Step 1, acetonitrile (35 mL) and an aqueous sodium hydroxide solution (0.25 mol/L, 28 mL, 6.94 mmol) were added, and the resulting mixture was stirred at room temperature for 6.5 hours. To the reaction mixture, water was added, and then, Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) was added thereto to neutralize the mixture, and the insoluble matter was removed by filtration. After the filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine and dried over sodium sulfate, and then, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=5/95 to 60/40), whereby Compound 8 (318 mg, quant.) was obtained.

Workup

  1. additionDowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) was added
  2. customthe insoluble matter was removed by filtration
  3. extractionAfter the filtrate was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=5/95 to 60/40)

Sources & evidence

ORD record
ord-c689a4df69de4233bbddf2bfa0f5c6c4
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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