Potassium Permanganate → HCID 66818525, compound

HRID 1024785Notes

Reaction equation

HRID 1024785 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=3)[CH:19]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:43].[K+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:16]2[CH:21]=[C:20]([CH:19]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[CH:17]=2)[O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([OH:43])=[O:30])=[CH:25][CH:24]=2)=[O:40])[CH2:10][CH2:9]1)=[O:41])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86665961HCID 86665961, compound

Product 1

HCID 66818525HCID 66818525, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.5 g (0.9 mmol) of {4-[3-(4-cyano-phenoxy)-5-(4-formyl-phenoxy)-benzoyl-amino]-cyclohexyl}-carbamic acid tert-butyl ester was dissolved in 15 ml of THF and 0.43 g (2.7 mmol) of potassium permanganate, dissolved in 8 ml of water, was added to THF solution at 10° C. during 10 min. The reaction mixture stirred over night at RT. Reaction progress was monitored by TLC. Reaction mixture was filtered through celite and washed with THF and thus obtained mother liquor was concentrated under vacuo. Product was crystallized with ethyl acetate to afford 0.25 g of the required product. 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.36 (9H, s), 1.78 (4H, m), 3.18 (1H, m), 3.66 (1H, m), 6.75 (1H, d), 6.94 (3H, m), 7.18 (2H, d), 7.36 (2H, s), 7.86 (4H, d), 8.38 (1H, d).

Workup

  1. customReaction progress
  2. customReaction mixture
  3. filtrationwas filtered through celite
  4. washwashed with THF and thus obtained mother liquor
  5. concentrationwas concentrated under vacuo
  6. customProduct was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-6cc772db99834a369f3b62b8686441df
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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