Trifluoroacetic acid → HCID 86601541, compound

HRID 2217565Notes

Reaction equation

HRID 2217565 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:35])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:17][C:16]=1[C:31]([F:34])([F:33])[F:32])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:30][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:35])=[C:16]([C:31]([F:34])([F:32])[F:33])[CH:17]=1)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68806200HCID 68806200, compound

Product 1

HCID 86601541HCID 86601541, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2′-Methanesulfonyl-3-trifluoromethyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.97 g, 1.9 mmol) was dissolved in 10 mL DCM and 5 mL trifluoroacetic acid and stirred at ambient temperature overnight and concentrated. Redissolved in 100 mL EtOAc and 100 mL sat. NaHCO3, separated layers, washed organics with brine, dried with MgSO4, filtered and concentrated to yield title compound as an oil (0.78 g, 100%) APCI (AP−): 411.0 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dissolutionRedissolved in 100 mL EtOAc
  3. custom100 mL sat. NaHCO3, separated layers
  4. washwashed organics with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c171fdc7a59940be826a941b04fd194c
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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