Trifluoroacetic acid → HCID 67776832, compound

HRID 1026273Notes

Reaction equation

HRID 1026273 reaction equation
[C:1]([NH:4][C@@H:5]([CH3:41])[CH2:6][O:7][C:8]1[CH:12]=[C:11]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]3[CH2:26][CH2:25]3)=[CH:18][C:17]=2[S:27]CCC(OCC(CC)CCCC)=O)=O)[O:10][N:9]=1)(=[O:3])[CH3:2].[O-]CC.[Na+].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C1COCC1>[CH:24]1([CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]3[N:15]=[C:13]([C:11]4[O:10][N:9]=[C:8]([O:7][CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:41])[CH:12]=4)[S:27][C:17]=3[CH:18]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 67778377HCID 67778377, compound

Product 1

HCID 67776832HCID 67776832, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-ethylhexyl 3-{[2-{[(3-{[(2S)-2-(acetylamino)propyl]oxy}isoxazol-5-yl)carbonyl]amino}-5-(cyclopropylmethoxy)phenyl]sulfanyl}propanoate (935 mg), sodium ethoxide (20% ethanol solution, 1.08 g) and THF (10 mL) was stirred at room temperature for 30 min. To the reaction mixture was added trifluoroacetic acid (0.611 mL) at 0° C., and the obtained mixture was stirred at 70° C. overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and recrystallized (ethyl acetate) to give the title compound as white crystals (71.6 mg).

Workup

  1. stirringthe obtained mixture was stirred at 70° C. overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  7. customrecrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-032194c44de74a64a2858d1626636c04
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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