Sodium Hydroxide → HCID 22675452, compound

HRID 1005960Notes

Reaction equation

HRID 1005960 reaction equation
[S:1]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[N:22](C(C)=C)[C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[O-][Mn](=O)(=O)=O.[K+].[OH-].[Na+]>CC(O)(C)C>[S:1]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[NH:22][C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 22675419HCID 22675419, compound

Product 1

HCID 22675452HCID 22675452, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.62 g of the compound obtained in Example 14b was dissolved in 10 ml of t-BuOH, added dropwise slowly with a mixed solution (30 ml) of 1.92 g of KMnO4 and 50 ml of 0.1 N NaOH, and then the mixture was stirred for 1 hour. The reaction mixture was extracted three times with chloroform, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 0.34 g of the title compound (yield: 61%).

Workup

  1. extractionThe reaction mixture was extracted three times with chloroform
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-7c56aafe74214fa384c7ee2b1528a553
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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