Trifluoroacetic acid → HCID 68487595, compound

HRID 1875099Notes

Reaction equation

HRID 1875099 reaction equation
C(O)(C(F)(F)F)=O.CC([N:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[C:19]([O:25][C:26]2[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[C:28]([Cl:34])[CH:27]=2)[C:18]=1[F:35])C(=O)[O-])(C)C>C(Cl)Cl>[NH2:12][CH2:16][C:17]1[C:18]([F:35])=[C:19]([O:25][C:26]2[CH:31]=[C:30]([CH:29]=[C:28]([Cl:34])[CH:27]=2)[C:32]#[N:33])[C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867616521,1-Dimethylethyl({3-[(3-chloro-5-cyanophenyl)oxy]-4-ethyl-2-fluorophenyl}methyl)carbamate

Product 1

HCID 68487595HCID 68487595, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.903 ml, 24.70 mmol) was added to a solution of 1,1-dimethylethyl({3-[(3-chloro-5-cyanophenyl)oxy]-4-ethyl-2-fluorophenyl}methyl)carbamate (0.5 g, 1.235 mmol) in DCM (30 mL) at RT under an atmosphere of nitrogen. After 16 h, the solution was concentrated under vacuum. Saturated NaHCO3 solution (100 mL) and ethyl acetate (100 mL) were added and the mixture was stirred for 1 h. The organic layer was separated, washed with water (100 mL), brine (100 mL), dried over Na2SO4, filtered and concentrated to give the title compound (0.38 g, >99%) as a brown oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.29-7.33 (m, 1H), 7.21-7.27 (m, 1H), 7.13 (t, 1H), 7.09 (d, 1H), 6.98 (s, 1H), 3.92 (s, 2H), 2.54 (d, 2H), 1.54 (d, 2H), 1.13-1.19 (m, 3H).

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. additionSaturated NaHCO3 solution (100 mL) and ethyl acetate (100 mL) were added
  3. customThe organic layer was separated
  4. washwashed with water (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-887f798b9c42427f8e7cd2b25ba7f8c9
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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