Trifluoroacetic acid → HCID 85836069, compound

HRID 2217422Notes

Reaction equation

HRID 2217422 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:31])[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][CH:16]=1)=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:31])=[CH:16][CH:17]=1)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68806643HCID 68806643, compound

Product 1

HCID 85836069HCID 85836069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2′-Methanesulfonyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.8 g, 1.7 mmol) was dissolved in 25 mL DCM and 5 mL trifluoroacetic acid and stirred at ambient temperature for one hour 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 (quant. yield) APCI (AP−): 343.1 (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-9850d7e9a70b4e3a864841b2b99c30a4
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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