Dimethyl Sulfoxide → HCID 57302665, compound

HRID 458048Notes

Reaction equation

HRID 458048 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][C@@H:8]([CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+].CS(C)=O>CCOC(C)=O>[C:1]([O:5][C:6](=[O:29])[CH2:7][C@@H:8]([CH2:17][N:30]=[N+:31]=[N-:32])[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 57186074HCID 57186074, compound

Product 1

HCID 57302665HCID 57302665, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Compound 159 (3.01 g, 7.05 mmol), sodium azide (1.26 g, 19.40 mmol) and DMSO (12 mL) were combined and heated to 60° C. for 3 hours. EtOAc (100 mL) was added to the reaction and filtered. The solids were washed with EtOAc (20 mL), and the filtrated evaporated. The crude material was chromatographed on silica eluting with 5% EtOAc/hexanes to give 160 as an oil (1.86 g, 89%).

Workup

  1. filtrationfiltered
  2. washThe solids were washed with EtOAc (20 mL)
  3. customthe filtrated evaporated
  4. customThe crude material was chromatographed on silica eluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-6cd09e04943545e3a4b3e165a00be062
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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