Sodium Azide → HCID 101160192, compound

HRID 1976770Notes

Reaction equation

HRID 1976770 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[OH:14])(=O)=O)=CC=1.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[N:27]([CH2:12][C@H:13]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[OH:14])=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 88223743HCID 88223743, compound

Product 1

HCID 101160192HCID 101160192, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution/slurry of Example 23C (450 mg; 1.2 mmol) and sodium azide (153 mg; 2.4 mmol) in DMF (5 mL) was heated at 80-90° C. for 2 hours, treated with brine, and extracted with ethyl acetate. The extract was washed with brine (2×), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 30% ethyl acetate/hexane) to provide 223 mg (75%).the desired product as a nearly colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash chromatography on silica gel with 30% ethyl acetate/hexane)
  7. customto provide 223 mg (75%)

Sources & evidence

ORD record
ord-6f31e4df667c4be0b082ed8c4ef58f14
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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