Hydrogen Peroxide → HCID 69588602, compound

HRID 1796864Notes

Reaction equation

HRID 1796864 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:10]([OH:16])[C:11]([O:13]CC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].OO.O.[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@H:10]([OH:16])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 90828402HCID 90828402, compound

Product 1

HCID 69588602HCID 69588602, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of Example 9C (0.316 g, 0.90 mmol), 30% hydrogen peroxide (0.40 mL, 3.5 mmol), and lithium hydroxide monohydrate (0.076 g, 1.8 mmol) in 3:1 tetrahydrofuran/water (8 mL) was stirred at 0° C. for 3 hours and concentrated. The concentrate was dissolved in water and the pH adjusted to 10 with 1M NaOH. The solution was washed twice with diethyl ether, adjusted to pH 2 with 1M HCl, and extracted twice with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 324 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in water
  3. washThe solution was washed twice with diethyl ether
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9ef5dc2f7a944a77a2207bccc2dd3963
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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