2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 66937496, compound

HRID 1515368Notes

Reaction equation

HRID 1515368 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][C:4]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:40])C=CC=CC=1>O1CCCC1>[CH3:16][O:15][C:13](=[O:14])[CH:12]([OH:40])[C:4]1[S:5][C:6]2[C:11]([C:2](=[O:1])[C:3]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 2733832Lithium HexamethyldisilazideHCID 66937667HCID 66937667, compound

Product 1

HCID 66937496HCID 66937496, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, the compound obtained in (1) above (0.16 mmol, 50 mg) was dissolved in tetrahydrofuran (3.0 mL), and the solution was cooled to −78° C. Then, 0.24 mL of lithium hexamethyldisilazide (a 1.0 M solution) was added thereto dropwise, and stirred for 10 min. A Davis reagent (0.32 mmol, 84 mg) was added to the resulting solution, and stirred for 30 min. After the disappearance of the starting materials was confirmed by thin-layer chromatography, the reaction was terminated by adding a saturated aqueous ammonium solution to the reaction solution. Then, the organic substances were extracted with ethyl acetate, and the obtained organic layer was dried over magnesium sulfate. The solvents were evaporated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (0.15 mmol, 50 mg) was obtained in a 95% yield.

Workup

  1. stirringstirred for 30 min
  2. customthe reaction was terminated
  3. additionby adding a saturated aqueous ammonium solution to the reaction solution
  4. extractionThen, the organic substances were extracted with ethyl acetate
  5. dry with materialthe obtained organic layer was dried over magnesium sulfate
  6. customThe solvents were evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-05692000f2c543bfab08bce76fd7a374
Source dataset
uspto-grants-2012_07
Patent number
US08222429B2

Reaction notes

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