Sodium Azide → HCID 22663498, compound

HRID 392642Notes

Reaction equation

HRID 392642 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][C@H:17]2[CH2:30][O:29][C:20]3[CH:21]=[CH:22][C:23]4[NH:24][C:25](=[O:28])[O:26][C:27]=4[C:19]=3[O:18]2)(=O)=O)=CC=1>CN(C)C=O>[N:1]([CH2:16][CH:17]1[CH2:30][O:29][C:20]2[CH:21]=[CH:22][C:23]3[NH:24][C:25](=[O:28])[O:26][C:27]=3[C:19]=2[O:18]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86759541HCID 86759541, compound

Product 1

HCID 22663498HCID 22663498, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium azide (0.86 g, 13.2 mmole) was added to a solution of [(8R)-2-oxo-2,3,7,8-tetrahydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl 4-methylbenzene-sulfonate (5.0 g, 13 mmole) in dimethylformamide (250 mL). The solution was heated at 70° C. for 9 hours. The solvent was then removed in vacuum and replaced with 300 mL of methylene chloride. The mixture was washed with 300 mL portions of water and saturated brine, dried over magnesium sulfate, filtered and evaporated in vacuum to a yellow solid. The crude solid was column chromatographed on silica gel with 3% methanol in methylene chloride to yield the (S)-enantiomer of the title compound as a white solid (2.86 g, 86%).

Workup

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with 300 mL portions of water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuum to a yellow solid
  6. customchromatographed on silica gel with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-d4de8824d0514d8cbff989eb571cf25c
Source dataset
uspto-grants-2004_10
Patent number
US06800648B2

Reaction notes

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