Hydrogen Peroxide → HCID 70029476, compound

HRID 1862549Notes

Reaction equation

HRID 1862549 reaction equation
OO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:12][C@@H:11]([CH2:19][CH:20]=[O:21])[O:10][C@H:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]4[O:28][CH2:29][CH2:30][O:31][C:23]=34)[C:8]=2[CH:32]=1.[OH:33]P([O-])(O)=O.[Na+].Cl([O-])=O.[Na+]>C(#N)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][C:15]([CH3:17])([CH3:18])[CH3:16])[CH2:12][C@@H:11]([CH2:19][C:20]([OH:33])=[O:21])[O:10][C@H:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]4[O:28][CH2:29][CH2:30][O:31][C:23]=34)[C:8]=2[CH:32]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86758887HCID 86758887, compound

Product 1

HCID 70029476HCID 70029476, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Aqueous hydrogen peroxide (30% by weight; 69 mL, 605 mmol) was added to a solution of [trans-7-chloro-5-(2,3-ethylenedioxyphenyl)-1-neopentyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]-acetaldehyde (250 mg, 582 mmol), aqueous sodium phosphate monobasic (63 mg in 1 mL water) and acetonitrile (1.25 mL). Sodium chlorite (1M in water; 640 mL, 640 mmol) was then added dropwise. After 45 minutes, the reaction mixture was quenched with saturated aqueous sodium sulfite, concentrated, taken up in water and extracted with ethyl acetate (3×). The combined organics were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (2% methanol/chloroform) to give 170 mg (66%) of the title compound as a white foam.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium sulfite
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash column chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-e3f87a46511f4103978e64c4219e39a8
Source dataset
uspto-grants-2003_03
Patent number
US06537987B1

Reaction notes

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