m-Chloroperbenzoic acid → HCID 58858025, compound

HRID 1162307Notes

Reaction equation

HRID 1162307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@@H:12]([C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:29][C:28]4=[CH:30][N:31]=[C:32]([CH3:33])[N:27]4[C:26]3=[O:34])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:14][S:15][CH3:16])=[O:10])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][C@@H:12]([C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:29][C:28]4=[CH:30][N:31]=[C:32]([CH3:33])[N:27]4[C:26]3=[O:34])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:14][S:15]([CH3:16])=[O:43])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58858000HCID 58858000, compound

Product 1

HCID 58858025HCID 58858025, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N—(4-chlorophenyl)—N′—((1R)-1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)-3-(methylthio)propyl)urea (0.21 g) obtained in Example 65 in dichloromethane (15 ml) was added 3-chloroperbenzoic acid (0.10 g), and mixed at 0° C. for 20 minutes. The reaction mixture was diluted with dichloromethane, washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1). The product was recrystallized from ethanol-diethyl ether to obtain the title compound as colorless powder (0.12 g, 54%).

Workup

  1. additionmixed at 0° C. for 20 minutes
  2. washwashed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1)
  6. customThe product was recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-57fd3820f4a6442a88ca339b80183a75
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…