Potassium Permanganate → HCID 69109367, compound

HRID 273427Notes

Reaction equation

HRID 273427 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[CH:10]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:37].[K+]>C1COCC1.O>[CH2:1]([O:8][C:9]([CH:10]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:37])=[O:26])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 72575121HCID 72575121, compound

Product 1

HCID 69109367HCID 69109367, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl ester 3 (4.6 g, 9.7 mmol) was dissolved in THF (100 mL) and the solution stirred at 70° C. Potassium permanganate (7.7 g, 48.5 mmol) dissolved in water (125 mL) was added slowly through a dropping funnel over a period of 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 (1×100 mL) and brine (1×100 mL), dried, and concentrated under reduced pressure to yield the desired acid compound 4 (4.5 g, 94%). 1H NMR (DMSO-d6): 12.7 (br, 1H), 7.91 (d, J=8.8 Hz, 2H), 7.42 (d, J=8.4 Hz), 7.30-7.37 (m, 7H), 7.03 (d, J=8.8 Hz, 2H), 6.97 (d, J=8.8 Hz, 2H), 5.12 (s, 2H), 4.24-4.28 (m, 1H), 3.04 (dd, J=13.6 and 5.2 Hz, 1H), 2.91 (dd, J=13.6 and 9.6 Hz, 1H), 1.33 (s, 9H).

Workup

  1. additionwas added slowly through a dropping funnel over a period of 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 (1×100 mL) and brine (1×100 mL)
  10. customdried
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f618d00494b24d3cb61b352a5634560e
Source dataset
uspto-grants-2008_11
Patent number
US07456292B2

Reaction notes

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