Dimethyl Sulfoxide → HCID 86584558, compound

HRID 1794772Notes

Reaction equation

HRID 1794772 reaction equation
Br[CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1)[OH:4].[I-].[Na+].[N-:18]=[N+:19]=[N-:20].[Na+].CS(C)=O>O>[N:18]([CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1)[OH:4])=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5238Sodium IodideHCID 33557Sodium AzideHCID 54577205HCID 54577205, compound

Product 1

HCID 86584558HCID 86584558, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-{4-[(1S)-2-bromo-1-hydroxyethyl]phenyl}methanesulfonamide (which was obtained in Example 112) (1.73 g, 5.9 mmol), sodium iodide (0.88 g, 5.9 mmol), sodium azide (1.53 g, 23.6 mmol), and methyl sulfoxide (15 mL) was stirred at ambient temperature for 7 days, poured into water and extracted with ethyl acetate. The organic extracts were washed with water, and dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/chloroform/isopropylalcohol,5/4.5/0.5) gave an off-white solid (0.56 g, 70% yield); MS (ES) m/z: 256 (M)+; 1H NMR (400 MHz, DMSO-d6) δ 2.94 (s, 3H), 3.30 (m, 2H), 4.74 (m, 1H), 5.75 (d, 1H), 7.17 (d, 2H), 7.32 (d, 2H), 9.67(s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialdried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/chloroform/isopropylalcohol,5/4.5/0.5)

Sources & evidence

ORD record
ord-9854d3a080eb4508be5f172ef722d03e
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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