Trifluoroacetic acid → HCID 178507476, compound

HRID 56626Notes

Reaction equation

HRID 56626 reaction equation
C(O)(C(F)(F)F)=O.[S:8]=[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)[NH:10]1>ClCCl>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[NH:10][C:9](=[S:8])[O:13][N:12]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452691HCID 178452691, compound

Product 1

HCID 178507476HCID 178507476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 0.8 ml of TFA was added to a solution of 119 mg (0.40 mmol) of tert-butyl [4-(5-thioxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]carbamate in 4 ml of dichlormethane, and the mixture was stirred at RT for 40 min. Subsequently, the reaction mixture was concentrated under reduced pressure. Ethyl acetate and a saturated aqueous sodium bicarbonate solution were added to the residue. After phase separation, the aqueous phase was extracted with ethyl acetate. The aqueous phase was concentrated and the crude product was purified by preparative HPLC (water/acetonitrile/0.1% formic acid gradient). Yield: 30 mg (38% of theory)

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate and a saturated aqueous sodium bicarbonate solution were added to the residue
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. concentrationThe aqueous phase was concentrated
  6. customthe crude product was purified by preparative HPLC (water/acetonitrile/0.1% formic acid gradient)

Sources & evidence

ORD record
ord-7b29cb89b3f749f18ebc48c38ece5169
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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