Hydrogen Peroxide → HCID 86650567, compound

HRID 1746149Notes

Reaction equation

HRID 1746149 reaction equation
[C:1]1([S:7][C:8]2[CH2:12][CH2:11][O:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:13]O.O.C(Cl)Cl>C(O)C.Cl>[C:1]1([S:7]([C:8]2[CH2:12][CH2:11][O:10][N:9]=2)=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 6344DichloromethaneHCID 11830021HCID 11830021, compound2×

Product 1

HCID 86650567HCID 86650567, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-(phenylsulfinyl)-4,5-dihydroisoxazole I-249a and I-249b were prepared by the oxidation of racemic 3-(phenylthio)-4,5-dihydroisoxazole I-248. 3-(Phenylthio)-4,5-dihydroisoxazole I-248 (1.0 equiv) was dissolved in ethanol (0.15 M) followed by the addition of excess hydrogen peroxide in water (30% by weight, >50 equiv) and 1N HCl (0.29 M). The reaction was stirred at room temperature for 14 h after which it was transferred to a separatory funnel with excess water and methylene chloride. The water layer was extracted with methylene chloride (1×), dried over magnesium sulfate, and concentrated to provide crude product that was recrystallized from hexanes to provide the desired racemic 3-(phenylsulfinyl)-4,5-dihydroisoxazole I-249. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=355.5 m/z. Activity: C

Workup

  1. extractionThe water layer was extracted with methylene chloride (1×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto provide crude product that
  5. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-cfb72bd1822d492aa5895f1e5c71ce47
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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