Hydrogen Peroxide → HCID 22621965, compound

HRID 840275Notes

Reaction equation

HRID 840275 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[C:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:20][CH2:19]3)[C:10]3=[N:11][CH:12]=[CH:13][C:14]([S:15][CH3:16])=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:33]=1.[OH:34]O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[C:18]3[CH2:19][CH2:20][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:22][CH2:23]3)[C:10]3=[N:11][CH:12]=[CH:13][C:14]([S:15]([CH3:16])=[O:34])=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:33]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 22621926HCID 22621926, compound

Product 1

HCID 22621965HCID 22621965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
73 °C

Procedure

To the title compound from Example 255 (0.18 grams) dissolved in anhydrous THF (10 mL) was added 30% aqueous hydrogen peroxide (3 mL) and the resulting solution was stirred for 12 hours at 73° C. The solution was concentrated in vacuo, diluted with CH2Cl2, and washed with water. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to afford the title compound after preparative plate chromatography (silica gel) using 3% MeOH-CH2Cl2 (0.04 grams, 26%, MH+ 492).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additiondiluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2fc980eead843be8aa31ba2f2b74d13
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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