Acetonitrile → HCID 68806200, compound

HRID 2217453Notes

Reaction equation

HRID 2217453 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:33])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2SC)=[CH:17][C:16]=1[C:29]([F:32])([F:31])[F:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:35][S:36]([O-:38])=O.[K+].[C:40](#N)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:33])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[S:36]([CH3:40])(=[O:38])=[O:35])=[CH:17][C:16]=1[C:29]([F:30])([F:31])[F:32])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 68805947HCID 68805947, compound

Product 1

HCID 68806200HCID 68806200, compound

Procedure

2-(2′-Methylsulfanyl-3-trifluoromethyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.8 g, 3.7 mmol) was dissolved in 20 mL acetonitrile, and added oxone (4.6 g, 6.8 mmol) in one portion and stirred at ambient temperature 4 days and then concentrated. Redissolved in 100 mL EtOAc and 100 mL sat. NaHCO3, separated layers, washed organics with brine, dried with MgSO4, filtered and concentrated. Purified on a silica gel column eluted with 20% EtOAc in hexanes. Combined and concentrated pure fractions to yield title compound. (1.05 g, 55%) APCI (AP−): 511.1 (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
  8. customPurified on a silica gel column
  9. washeluted with 20% EtOAc in hexanes
  10. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-ba937caa73cb43a497c10d82d3d6187f
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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