Hydrogen Peroxide → HCID 87735465, compound

HRID 902936Notes

Reaction equation

HRID 902936 reaction equation
[CH2:1]([O:8][P:9]([CH2:19][CH2:20][CH2:21][C:22](N1C(CC2C=CC=CC=2)COC1=O)=[O:23])(=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.[OH2:39].[OH-:40].[Li+].S([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:12]([O:39][C:1](=[O:8])[CH2:2][CH:21]([CH2:20][CH2:19][P:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:18])[C:22]([OH:23])=[O:40])([CH3:17])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 87735523HCID 87735523, compound

Product 1

HCID 87735465HCID 87735465, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of the compound of example 76 (1.03 g, 1.66 mmol) in a mixture of THF/water (4:1, 20 mL) was cooled in an ice bath and treated drop wise with a hydrogen peroxide solution (30%, 0.7 mL). After 5 minutes, a solution of lithium hydroxide monohydrate (1M, 6.6 mL, 6.6 mmol) was added over a period of 10 minutes. The reaction was completed following 2 h of stirring in the ice bath. At this stage, an aqueous solution of sodium sulfite (850 mg, 6.64 mmol, 5 mL) was added. The ice bath was removed and the reaction mixture was stirred for another 30 minutes. Most of the solvent was removed by evaporation and the residue was extracted with ether. The alkaline phase was acidified with HCl (6M) to pH˜1 and extracted three times with ethyl acetate. The recombined organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The desired product was obtained as a colorless oil. 1H-NMR (CDCl3, 400 MHz: 1.40(s, 9H); 1.85(m, 4H); 2.27, 2.58(2dd, J1=16.5 Hz. J2=5.6 Hz, 4H); 2.84(m, 1H); 4.98(m, 4H); 7.31(m, 10H). 31P-NMR (CDCl3, 400 MHz): 33.14.

Workup

  1. temperaturewas cooled in an ice bath
  2. waitThe reaction was completed following 2 h
  3. customThe ice bath was removed
  4. customMost of the solvent was removed by evaporation
  5. extractionthe residue was extracted with ether
  6. extractionextracted three times with ethyl acetate
  7. washThe recombined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-2ca27353aa314194bc94796431e6fce5
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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