Trifluoroacetic acid → HCID 57418370, compound

HRID 1868140Notes

Reaction equation

HRID 1868140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([CH:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[C@H:10]([CH3:36])[CH2:9]2)=[C:4]([C:37]([F:40])([F:39])[F:38])[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:36])[CH2:9]2)=[C:4]([C:37]([F:40])([F:38])[F:39])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57418369HCID 57418369, compound

Product 1

HCID 57418370HCID 57418370, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenyl]piperidine-1-carboxylate (540 mg, 0.923 mmol) in DCM (15 mL) was added TFA (5 mL). The reaction mixture was stirred at room temperature for 2 h and washed with aq. Na2CO3. The organic layer was dried over Na2SO4, concentrated and redissolved in Et2O and acidified with 1N HCl in Et2O to give the titled compound as a white solid (427 mg, 89%). HRMS: calcd for C23H27F4N3O2S+H+, 486.18328. found (ESI-FTMS, [M+H]1+), 486.18382.

Workup

  1. washwashed with aq. Na2CO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionredissolved in Et2O

Sources & evidence

ORD record
ord-5c4bf6f5eb0c4e0b875533e3b7b333f5
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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