Acetonitrile → HCID 68806643, compound

HRID 2217421Notes

Reaction equation

HRID 2217421 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:29])[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][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:31][S:32]([O-:34])=O.[K+].[C:36](#N)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:29])[NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[S:32]([CH3:36])(=[O:34])=[O:31])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 68808158HCID 68808158, compound

Product 1

HCID 68806643HCID 68806643, compound

Procedure

2-(2′-Methylsulfanyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 2.4 mmol) was dissolved in 10 mL acetonitrile, added oxone (2.98 g, 4.8 mmol) in one portion and stirred at ambient temperature for 1 week 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% moving to 40% EtOAc in hexanes. Combined and concentrated pure fractions to yield title compound. (0.80 g, 75%) APCI (AP−): 443.1 (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%
  10. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-07a8b78193c945898c4e82190584d33e
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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