Hydrogen Peroxide → HCID 15488980, compound

HRID 720512Notes

Reaction equation

HRID 720512 reaction equation
[CH2:1]([C@:3]1([OH:29])[C:26]2[CH:25]=[C:24]3[N:10]([CH2:11][C:12]4[C:13]3=[N:14][C:15]3[CH:16]=[C:17]([F:23])[C:18]([F:22])=[CH:19][C:20]=3[CH:21]=4)[C:9](=[O:27])[C:8]=2[CH2:7][O:6][C:5](=[O:28])[CH2:4]1)[CH3:2].[CH:30](=O)[CH2:31][CH2:32][CH2:33]C.OO>O.S(=O)(=O)(O)O>[CH2:30]([C:21]1[C:20]2[CH:19]=[C:18]([F:22])[C:17]([F:23])=[CH:16][C:15]=2[N:14]=[C:13]2[C:24]3[N:10]([CH2:11][C:12]=12)[C:9](=[O:27])[C:8]1[CH2:7][O:6][C:5](=[O:28])[CH2:4][C@@:3]([CH2:1][CH3:2])([OH:29])[C:26]=1[CH:25]=3)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 8063PentanalHCID 219023diflomotecan

Product 1

HCID 15488980HCID 15488980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

The product of Stage 95d (100 mg; 0.25 mmol) is dissolved in a mixture of water (1.33 ml) and sulphuric acid at 95% (1 ml). Heptahydrated iron (III) sulphate (28 mg; 0.10 mmol); valeraldehyde (0.17 ml; 1.60 mmol) are added to this solution and the resulting solution is cooled down with an ice bath. The reaction medium is then treated dropwise with hydrogen peroxide at 30% (0.38 ml; 1 mmol); agitated for 5 hours at ambient temperature, then diluted with water (50 ml) and extracted with dichloromethane (4×50 ml). The combined extracts are washed with water and with a saturated aqueous solution of sodium chloride, then dried over magnesium sulphate and concentrated under reduced pressure. The residue is purified by chromatography at medium pressure (SiO2, MeOH/CH2Cl2, 5/95) in order to produce the expected solid (m.p.>275° C.).

Workup

  1. temperaturethe resulting solution is cooled down with an ice bath
  2. extractionextracted with dichloromethane (4×50 ml)
  3. washThe combined extracts are washed with water and with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography at medium pressure (SiO2, MeOH/CH2Cl2, 5/95) in order

Sources & evidence

ORD record
ord-d15da8fd20bd40bd923ec8071d975120
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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