Acetonitrile → HCID 68806643, compound

HRID 1796251Notes

Reaction equation

HRID 1796251 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-ce409f9ab64f494dbcfe3396d665f6b2
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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