Trifluoroacetic acid → HCID 15390172, compound

HRID 1289084Notes

Reaction equation

HRID 1289084 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

In 10 ml of methylene chloride, 1.2 g of 2-(1-hydroxy-1,3-dimethylbutyl)-3-t-butoxycarbonylaminothiophene was dissolved, 0.44 g of triethylsilane and 4.3 g of trifluoroacetic acid were added, and the mixture was stirred at the room temperature for 20 hours. The reaction mixture was 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 magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain 0.43 g of the product as a crystal.

Workup

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

Sources & evidence

ORD record
ord-87a229de2db3485d8f4bcc50ccec1b56
Source dataset
uspto-grants-1998_05
Patent number
US05747518

Reaction notes

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