Water → HCID 12415357, compound

HRID 1746150Notes

Reaction equation

HRID 1746150 reaction equation
[C:1]1([S:7]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:22])C=1.O>C(Cl)Cl>[C:1]1([S:7]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)(=[O:22])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 86650567HCID 86650567, compound2×

Product 1

HCID 12415357HCID 12415357, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(phenylsulfonyl)-4,5-dihydroisoxazole I-250a and I-250b were prepared by the oxidation of racemic 3-(phenylsulfinyl)-4,5-dihydroisoxazole I-249. 3-(Phenylsulfinyl)-4,5-dihydroisoxazole I-249 is dissolved in methylene chloride (0.03 M). m-Chloroperbenzoic acid (77% by weight, 2.95 equiv) are added in two portions and the reaction is allowed to stir at room temperature for 14 h after which it is transferred to a separatory funnel with excess water and methylene chloride. The organic layer is washed with saturated sodium bicarbonate (2×), dried over magnesium sulfate, and concentrated to provide crude solid that is recrystallized from methylene chloride/hexanes to provide the desired racemic 3-(phenylsulfonyl)-4,5-dihydroisoxazole I-250. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=371.7 m/z. Activity: C

Workup

  1. washThe organic layer is washed with saturated sodium bicarbonate (2×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto provide crude solid
  5. customthat is recrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-fe222176308341b886340bd746cb2df7
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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