Potassium Permanganate → HCID 69205989, compound

HRID 273434Notes

Reaction equation

HRID 273434 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:32].[K+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:7][CH:8]([C:25](=[O:29])[N:26]([CH3:27])[CH3:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([OH:32])=[O:24])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)=[O:30])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 72575120HCID 72575120, compound

Product 1

HCID 69205989HCID 69205989, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Amide compound 10 (2.0 g, 4.85 mmol) was dissolved in THF (50 mL) and the solution stirred at 70° C. Potassium permanganate (3.06 g, 19.4 mmol) dissolved in water (50 mL) was added slowly through a dropping funnel (5 mL/min) over 2 hours. After addition was complete, reaction mixture was stirred at 70° C. for 30 min and cooled to room temperature. The brown precipitate was filtered over a Celite® bed and the filtrate was concentrated under reduced pressure. The residual oil was taken up in EtOAc (100 mL) and acidified with 2.0 M HCl. The organic layer was separated and washed with water (1×50 mL) and brine (1×50 mL), dried, and concentrated under reduced pressure to yield the desired acid compound 11 (1.9 g, 91%). 1H NMR (DMSO-d6): 12.7 (br, 1H), 7.91 (d, J=8.8 Hz, 2H), 7.33 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.8 Hz, 1H), 7.04 (d, J=8.4 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 4.56 (ddd, J=13.6, 9.2, and 6.0 Hz, 1H), 2.93 (s, 3H), 2.74-2.91 (m, 5H), 1.31 (s, 9H).

Workup

  1. additionwas added slowly through a dropping funnel (5 mL/min) over 2 hours
  2. additionAfter addition
  3. customreaction mixture
  4. stirringwas stirred at 70° C. for 30 min
  5. temperaturecooled to room temperature
  6. filtrationThe brown precipitate was filtered over a Celite® bed
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe organic layer was separated
  9. washwashed with water (1×50 mL) and brine (1×50 mL)
  10. customdried
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f07846e100544bd1967a0207f9af9923
Source dataset
uspto-grants-2008_11
Patent number
US07456292B2

Reaction notes

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