Trifluoroacetic acid → HCID 57418404, compound

HRID 1868156Notes

Reaction equation

HRID 1868156 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[C:28]([F:31])([F:30])[F:29])[CH2:17][C@H:16]2[CH3:32])(=[O:14])=[O:13])=[C:8]([F:33])[CH:7]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:33][C:8]1[CH:7]=[C:6]([OH:5])[CH:11]=[CH:10][C:9]=1[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[C:28]([F:30])([F:29])[F:31])[CH2:17][C@H:16]1[CH3:32])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44248452HCID 44248452, compound

Product 1

HCID 57418404HCID 57418404, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-1-[(4-tert-butoxy-2-fluorophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazine (375 mg, 0.76 mmol) in DCM (25 mL) was added TFA (5 mL). The reaction was allowed to stir for 1 hour, after which it was judged complete by LCMS. The reaction was concentrated in vacuo to remove excess TFA, and the crude oil was dissolved in DCM (20 mL) and washed with saturated NaHCO3(aq) (3×25 mL). The organic phase was dried over Na2SO4, and decanted, then concentrated in vacuo affording the desired phenol in >95% purity, which was used in subsequent synthetic steps without purification. HRMS: calcd for C18H17F5N2O3S+H+, 437.09528. found ([M+H]+), 437.09527.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove excess TFA
  3. dissolutionthe crude oil was dissolved in DCM (20 mL)
  4. washwashed with saturated NaHCO3(aq) (3×25 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customdecanted
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c2776ceee1c492d94422f2a75d982c1
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…