Potassium Permanganate → HCID 54285194, compound

HRID 2268634Notes

Reaction equation

HRID 2268634 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:34])[N:25]([CH2:31]C=C)[CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.[Mn]([O-])(=O)(=O)=O.[K+].I([O-])(=O)(=O)=O.[Na+].[C:48](=O)([OH:50])[O-:49].[Na+]>C(O)(C)(C)C.O.C(O)C>[Cl:23][C:21]1[CH:20]=[C:19]([CH:18]=[C:17]([O:16][CH2:15][CH2:14][NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:22]=1)[C:24]([N:25]([CH2:31][C:48]([OH:50])=[O:49])[CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:34]

Participants

8

Reactant 4

HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 18349220{2-[3-(Allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl esterHCID 23667635Sodium periodate

Product 1

HCID 54285194HCID 54285194, compoundYield 41.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of {2-[3-(allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.06 g) in tert-butanol (3.2 ml) was added a solution of potassium permanganate (0.006 g), sodium periodate (0.157 g) and sodium bicarbonate (0.051 g) in water (3.2 ml). The purple reaction mixture was stirred at room temperature for 1.5 h and then added to ethanol (25 ml) the precipitate was filtered and the filtrate evaporated in vacuo. The residue was dissolved in a mixture of dichloromethane (5 ml) and trifluoroacetic acid (5 ml) was stored at room temperature for 17 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.021 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure.

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was dissolved in a mixture of dichloromethane (5 ml) and trifluoroacetic acid (5 ml)
  4. waitwas stored at room temperature for 17 h
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c907fba1365d48ac902a57bf36f12124
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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