Trifluoroacetic acid → (2S,4R)-1-(2,5-Dimethyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697589Notes

Reaction equation

HRID 1697589 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])(=[O:19])=[O:18])[CH2:14][N:13]1[C:30](=S)[CH2:31][C:32](=[N:34][N:35](C(OC(C)(C)C)=O)[CH3:36])[CH3:33])=[O:11].C(OC(C)=O)(C)C>ClCCl>[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:28])([F:29])[F:27])(=[O:19])=[O:18])[CH2:14][N:13]1[C:30]1[N:35]([CH3:36])[N:34]=[C:32]([CH3:33])[CH:31]=1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7915Isopropyl AcetateHCID 86646836(2S,4R)-1-[3-(tert-Butoxycarbonyl-methyl-hydrazono)-thiobutyryl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770795(2S,4R)-1-(2,5-Dimethyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl EsterYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (61 ul, 0.8 mmol) was added to a solution of (2S,4R)-1-[3-(tert-butoxycarbonyl-methyl-hydrazono)-thiobutyryl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (90 mg, 160 umol) in dichloromethane (0.3 ml) under an argon atmosphere. The mixture was stirred at ambient temperature for 72 h. Ice water/10% aqueous sodium carbonate solution 1/1 and iPrOAc were added and the layers were separated. The aqueous layer was extracted four more times with iPrOAc, the combined organic layers were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown oil which was purified by preparative thin layer chromatography (silica gel, iPrOAc) to obtain the title compound (20 mg, 46 umol; 29%) as yellow solid. MS (ESI): m/z=432.1 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted four more times with iPrOAc
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto give a brown oil which
  7. customwas purified by preparative thin layer chromatography (silica gel, iPrOAc)

Sources & evidence

ORD record
ord-a0560819699146e7bcbd8935d50a7777
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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