Trifluoroacetic acid → HCID 15390172, compound

HRID 362175Notes

Reaction equation

HRID 362175 reaction equation
O[C:2]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[NH:13]C(OC(C)(C)C)=O)([CH3:7])[CH2:3][CH:4]([CH3:6])[CH3:5].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:13][C:12]1[CH:11]=[CH:10][S:9][C:8]=1[CH:2]([CH3:7])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 54419340HCID 54419340, compound

Product 1

HCID 15390172HCID 15390172, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 1.2 g of 2-(1-hydroxy-1,3-dimethylbutyl)-3-t-butoxycarbonylaminothiophene in 10 ml of methylene chloride, 0.44 g of triethylsilane and 4.3 g of trifluoroacetic acid were added. The mixture was stirred at room temperature for 20 hours, neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.43 g of the desired product as a crystal. 1H-NMR(270 MHz, CDCl3, δppm, J:Hz):0.89(3H,d,J=6.6), 0.90(3H,d,J=6.6), 1.23(3H,d,J=6.6),1.35-1.65(3H,m), 2.95(1H, sextet, J=6.6), 3.35(2H,brs), 6.55(1H,d,J=5.1), 6.95(1H,d,J=5.1)

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-87785170eb8e427ab68d90e2b198af06
Source dataset
uspto-grants-1999_02
Patent number
US05869427

Reaction notes

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