Trifluoroacetic acid → HCID 59253163, compound

HRID 386893Notes

Reaction equation

HRID 386893 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[O:19][N:18]=[C:17]([C:20]([CH3:28])([CH3:27])[CH2:21][N:22]([C:24](=[O:26])[CH3:25])[CH3:23])[CH:16]=1)(C)(C)C>C(Cl)Cl>[NH2:14][C:15]1[O:19][N:18]=[C:17]([C:20]([CH3:28])([CH3:27])[CH2:21][N:22]([CH3:23])[C:24](=[O:26])[CH3:25])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59253270HCID 59253270, compound

Product 1

HCID 59253163HCID 59253163, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.108 mL, 1.4 mmol) is added to a solution of {3-[2-(acetyl-methyl-amino)-1,1-dimethyl-ethyl]isoxazol-5-yl}-carbamic acid tert-butyl ester (87.0 mg, 0.28 mmol) in DCM (1 mL). The reaction mixture is stirred at room temperature for 1 h. More trifluoroacetic acid (0.20 mL, 2.59 mmol) is added to the reaction mixture and the reaction mixture is stirred for another hour. After this time, the reaction mixture is diluted with DCM and quenched with saturated aqueous NaHCO3 solution. The layers are separated and the aqueous layer is extracted with DCM twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide 28.0 mg of the title compound. Yield: 47%. LC-MS Retention time: 0.94 mins. ESI+ion mode. Zorbax SB-C18 column (3.5 μm, 4.6×30 mm). Gradient: 5% B to 80% B (0 min to 1.7 mins), 80% B to 95% B (1.7 mins to 2 mins), 95% B to 95% B (2 mins to 2.1 mins). Flow rate: 2.5 mL/min. A=(Water+0.1% Formic Acid) B=(Acetonitrile+0.1% Formic Acid). Diode Array Detector; m/z 212 [M+H].

Workup

  1. stirringthe reaction mixture is stirred for another hour
  2. customquenched with saturated aqueous NaHCO3 solution
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with DCM twice
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1effd129959e4dbcb4d7f89eed458d42
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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