m-Chloroperbenzoic acid → HCID 68807292, compound

HRID 2217425Notes

Reaction equation

HRID 2217425 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:30])[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[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:32]1C=C(C=CC=1)C(OO)=O.O[O:43][S:44]([O-:46])=O.[K+]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:30])[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:44]([CH3:32])(=[O:46])=[O:43])=[CH:17][C:16]=1[CH3:29])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23707502Potassium hydroxy sulfiteHCID 68805998HCID 68805998, compound

Product 1

HCID 68807292HCID 68807292, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Methyl-2′-methylsulfanyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 1.3 mmol) was dissolved in 10 mL EtOAc, added m-chloroperoxybenzoic acid (1.76 g, 6.1 mmol) in one portion and stirred at ambient temperature for 3 hours. Reaction not complete. Concentrated and redissolved in 10 mL acetonitrile and added oxone (1.5 g, 2.4 mmol) in one portion and stirred at ambient temperature overnight 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. (0.44 g, 72%) APCI (AP−): 457.1 (M−H)−.

Workup

  1. customReaction not complete
  2. concentrationConcentrated
  3. dissolutionredissolved in 10 mL acetonitrile
  4. stirringstirred at ambient temperature overnight
  5. concentrationconcentrated
  6. dissolutionRedissolved in 100 mL EtOAc
  7. custom100 mL sat. NaHCO3, separated layers
  8. washwashed organics with brine
  9. dry with materialdried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurified on a silica gel column
  13. washeluted with 20%
  14. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-e7e2000364b6419fa51b720d6e52aab5
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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