Trifluoroacetic acid → HCID 69648874, compound

HRID 1744494Notes

Reaction equation

HRID 1744494 reaction equation
C([CH:3]([C:26]([OH:28])=[O:27])[N:4]([C:19](OC(C)(C)C)=O)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:7]([C:17]#[N:18])[CH:6]=1)C.F[C:30](F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH2:19]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:7]([C:17]#[N:18])[CH:6]=1)[CH2:3][C:26]([OH:28])=[O:27])[CH3:30]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 22228079HCID 22228079, compound

Product 1

HCID 69648874HCID 69648874, compound

Procedure

To dimethylformamide solution (240 ml) containing N-(3-cyano-4-neopentyloxyphenyl)-tert-butoxycarboxamide (24.5 g) was added sodium hydride (60% content, 1.15 g) under ice-cooling and the mixture was stirred for 30 min. The mixture was warmed to room temperature and stirred further for 1 h. The reaction mixture was ice-cooled and ethyl bromoacetate (24.5 g) was added, which was followed by stirring for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 0.1N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform) to give ethyl N-tert-butoxycarbonyl-N-(3-cyano-4-neopentyloxyphenyl)glycine (36.5 g) as an oily substance. The obtained ethyl N-tert-butoxycarbonyl-N-(3-cyano-4-neopentyloxyphenyl)glycine (8.2 g) was added to trifluoroacetic acid (24 ml) at room temperature and the mixture was stirred for 1 h. The reaction mixture was poured into an aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated. The residue was purified by silica gel column chromatography (mobile phase: chloroform) to give the title compound (5.9 g), melting point: 78° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform)

Sources & evidence

ORD record
ord-745bf893552d46d09639f65421a24dd9
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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