Hydrogen Peroxide → HCID 66911535, compound

HRID 1967435Notes

Reaction equation

HRID 1967435 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[C@H:14]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH2:15]C(N1[C@H](C2C=CC=CC=2)COC1=O)=O.[OH:40]O.[OH-].[Li+].S([O-])([O-])=O.[Na+].[Na+].C1[CH2:54][O:53]CC1>O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[C@H:14]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)[CH2:15][C:54]([OH:53])=[O:40]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 67056229HCID 67056229, compound

Product 1

HCID 66911535HCID 66911535, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 22 (0.55 g, 1.0 mmol) in a mixture of THF (12 mL) and water (4 mL) at 0° C. was added hydrogen peroxide (0.41 mL, 30% in water), followed by lithium hydroxide (48 mg, 2.0 mmol) in water (2.5 mL). The reaction solution was stirred at 0° C. for 1 h and room temperature for 30 min. A solution of sodium sulfite (0.78 g) in water (5 mL) was then added. After stirring at 0° C. for 10 min, the mixture was concentrated in vacuo to remove the organic solvent. The remaining aqueous solution was diluted with aqueous sodium hydroxide and extracted with dichloromethane. The basic aqueous layer was separated, neutralized with aqueous ammonium chloride to pH 6-7 and then extracted with dichloromethane (3×). The combined organic extract was dried over sodium sulfate and concentrated in vacuo to give Compound 23 (0.41 g, crude), which was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 7.56-7.70 (m, 4H), 7.48-7.33 (m, 3H), 7.13 (d, J=2.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 1H), 6.80 (dd, J=9.0, 3.0 Hz, 1H), 6.08 (s, 1H), 5.18 (dd, J=9.0, 7.0 Hz, 1H), 4.21-4.00 (m, 4H), 3.77 (s, 3H), 3.20 (dd, J=16.0, 9.0 Hz, 1H), 3.12 (dd, J=16.0, 7.0 Hz, 1H).

Workup

  1. stirringAfter stirring at 0° C. for 10 min
  2. concentrationthe mixture was concentrated in vacuo
  3. customto remove the organic solvent
  4. additionThe remaining aqueous solution was diluted with aqueous sodium hydroxide
  5. extractionextracted with dichloromethane
  6. customThe basic aqueous layer was separated
  7. extractionextracted with dichloromethane (3×)
  8. extractionThe combined organic extract
  9. dry with materialwas dried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15a34f53d8c04f89bd4797efc7c256d8
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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