Tetrabutylammonium permanganate → HCID 19072548, compound

HRID 1955741Notes

Reaction equation

HRID 1955741 reaction equation
[C:1]1([CH3:38])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11](=[O:37])[CH:12]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[C:29]([CH:30]=[O:31])=[C:28]([Cl:32])[N:27]=[C:26]3[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:20][CH:19]=2)[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=[O:40].C([N+](CCCC)(CCCC)CCCC)CCC>N1C=CC=CC=1>[C:1]1([CH3:38])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C:11](=[O:37])[CH:12]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[C:29]([C:30]([OH:40])=[O:31])=[C:28]([Cl:32])[N:27]=[C:26]3[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:20][CH:19]=2)[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11760202Tetrabutylammonium permanganateHCID 19072485N-4-Tolylsulphonyl-2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)-phenyl]-2-cyclopentyl-acetamide

Product 1

HCID 19072548HCID 19072548, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

250 mg (0.45 mmol) of the compound from Example III are dissolved in 2.5 ml (0.45 mmol) of pyridine and 162 mg of tetrabutylammonium permanganate, dissolved in 1.5 ml of pyridine, are added at 60° C., and the mixture is stirred at 60° C. for 2 h. The pyridine is evaporated, and the residue is taken up in water, acidified with dilute HCl and extracted with ethyl acetate. The organic phase is concentrated and the residue is chromatographed on silica gel 60 using CH2Cl2 /MeOH (10:1).

Workup

  1. additionare added at 60° C.
  2. customThe pyridine is evaporated
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase is concentrated
  5. customthe residue is chromatographed on silica gel 60 using CH2Cl2 /MeOH (10:1)

Sources & evidence

ORD record
ord-f55a8a9747e94994b369373934dccc4c
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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