Trifluoroacetic acid → HCID 86592420, compound

HRID 1744692Notes

Reaction equation

HRID 1744692 reaction equation
FC(F)(F)C(O)=O.[C:8]([N:12]([CH2:18]OC)[CH2:13][Si](C)(C)C)([CH3:11])([CH3:10])[CH3:9].[F:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:8]([N:12]1[CH2:13][C@@H:28]([C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)[C@H:29]([C:30]([O:32][CH3:33])=[O:31])[CH2:18]1)([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 958751methyl (2E)-3-(4-fluorophenyl)prop-2-enoateHCID 22228418N-tert-Butyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine

Product 1

HCID 86592420HCID 86592420, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (38.9 mL, 0.505 mmol) was added to a solution of the product of step B (1.03 g, 5.05 mmol) and methyl (2E)-3-(4-fluorophenyl)prop-2-enoate (1.00 g, 5.05 mmol) in methylene chloride (10 mL) at ambient temperature. After 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–9% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent) furnished the title compound as a colorless liquid (1.06 g).

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–9% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent)

Sources & evidence

ORD record
ord-e1d51316040243d6ac2abe77288c2235
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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