Water → HCID 59434119, compound

HRID 508000Notes

Reaction equation

HRID 508000 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([N:24]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:25]1[CH:32]=[C:31]([F:33])[C:28]([CH:29]=O)=[C:27]([F:34])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[CH2:35]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:25]1[CH:32]=[C:31]([F:33])[C:28](/[CH:29]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:27]([F:34])[CH:26]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 10735667HCID 10735667, compound

Product 1

HCID 59434119HCID 59434119, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of ethyl diethylphosphonoacetate (7.71 g, 34.4 mmol) in tetrahydrofuran (80 mL) was added sodium hydride (60% in oil, 1.38 g, 34.4 mmol) and the mixture was stirred for 30 min. A solution of 4-(dibenzylamino)-2,6-difluorobenzaldehyde (9.28 g, 27.5 mmol) synthesized according to the method described in European Journal of Medicinal Chemistry, 1999, vol. 34, pp. 137-151 in tetrahydrofuran (100 mL) was added dropwise. The mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=97/3-hexane/ethyl acetate=60/40) to give the title compound (9.57 g, yield 85%) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=97/3-hexane/ethyl acetate=60/40)

Sources & evidence

ORD record
ord-54b336e06e6542f1b4290685802498fe
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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