Water → HCID 11823843, compound

HRID 263440Notes

Reaction equation

HRID 263440 reaction equation
C(=O)([O-])O.[Na+].[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14]([O:18][C:19]([CH2:21][C@@H:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:23]([OH:25])=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].O>CN(C)C=O>[CH2:6]([O:25][C:23]([C@H:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])=[O:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 10681747HCID 10681747, compound

Product 1

HCID 11823843HCID 11823843, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydrogencarbonate (305 mg) and benzyl bromide (1.0 ml) were added Successively to a solution of 2-(R)-(tert-butoxycarbonylmethyl)heptanoic acid (440 mg), prepared in Referential Example 5, in 18 ml of dimethylformamide (DMF), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extract was successively washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After the solvent had been distilled off under reduced pressure, the residue was purified by column chromatography through silica gel, using a 20:1 mixture of hexane and ethyl acetate as an eluent, to give 476 mg of the desired compound as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas successively washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. distillationAfter the solvent had been distilled off under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel
  7. additiona 20:1 mixture of hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-82680babbba54de1a3c3054b8f299246
Source dataset
uspto-grants-1997_07
Patent number
US05643908

Reaction notes

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