Dimethylformamide → HCID 10863050, compound

HRID 1826076Notes

Reaction equation

HRID 1826076 reaction equation
CCOC([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:20][CH3:21])=[C:14]([CH2:16][C:17]([OH:19])=O)[CH:15]=1)=O.[F:22][C:23]([F:32])([F:31])[C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.C(N(CC)CC)C.P(C#N)([O:45][CH2:46][CH3:47])(OCC)=O.CN(C)[CH:52]=[O:53]>>[CH2:7]([CH:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:20][CH3:21])=[C:14]([CH2:16][C:17](=[O:19])[NH:28][C:27]2[CH:29]=[CH:30][C:24]([C:23]([F:31])([F:32])[F:22])=[CH:25][CH:26]=2)[CH:15]=1)[C:52]([O:45][CH2:46][CH3:47])=[O:53])[CH3:6]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 76257Diethyl cyanophosphonateHCID 68848634HCID 68848634, compound

Product 1

HCID 10863050HCID 10863050, compoundYield 28%

Procedure

2-[5-(2-Ethoxycarbonyl)butyl-2-methoxyphenyl]acetic acid (500 mg, 1.70 mmol), 4-trifluoromethylaniline (300 mg, 1.86 mmol), triethylamine (260 μL, 1.87 mmol) and dehydrated N,N-dimethylformamide (6 mL) were mixed and, under an argon atmosphere, stirring and cooling with ice, diethyl cyanophosphate (283 μL, 1.87 mmol) was added. After stirring for 6 hours at room temperature, the mixture was allowed to stand overnight. Ice water was added to the reaction mixture, which was then extracted with ethyl acetate. The extracte was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=6:1 v/v) to afford 210 mg (28%) of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. stirringAfter stirring for 6 hours at room temperature
  3. extractionwas then extracted with ethyl acetate
  4. washThe extracte was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=6:1 v/v)

Sources & evidence

ORD record
ord-4da07acf4608465292dbe04ecccfcdad
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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