Trifluoroacetic acid → HCID 89444390, compound

HRID 2277758Notes

Reaction equation

HRID 2277758 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][S:9][CH2:10][C:11]1[CH:12]=[C:13]([NH:21]C(=O)OC(C)(C)C)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1>C(Cl)Cl>[CH3:8][S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=1)[NH2:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89451546HCID 89451546, compound

Product 1

HCID 89444390HCID 89444390, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.5 ml) was added to a stirred solution of tert-butyl {3-[(methylsulfanyl)methyl]-5-(tri-fluoromethyl)phenyl}carbamate (502 mg; 1.56 mmol) in DCM (5 mL) at 0° C. The ice bath was removed and the mixture was stirred for 45 min at RT. The batch was concentrated and saturated aqueous sodium bicarbonate solution was added. The batch was extracted with ethyl acetate (2×). The combined organic phases were dried (sodium sulfate), filtered and concentrated to give the crude product (336 mg), that was used without further purification.

Workup

  1. customThe ice bath was removed
  2. concentrationThe batch was concentrated
  3. additionsaturated aqueous sodium bicarbonate solution was added
  4. extractionThe batch was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic phases were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d12effc2322f4b3991c453db04a964a3
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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