Sodium Azide → HCID 18594802, compound

HRID 2071339Notes

Reaction equation

HRID 2071339 reaction equation
CS(O[CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O>[N:31]([CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18594876HCID 18594876, compound

Product 1

HCID 18594802HCID 18594802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.35 g. of ethyl 15-methanesulfonyloxy 9-oxo-prostanoate (Example 90) in 60 ml. of N,N-dimethylformamide containing 1.25 g. of sodium azide is heated on the steam-bath for 18 hours. The cooled solution is poured into 300 ml. of water and the resulting mixture is extracted several times with ether. The combined ether extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness. The residual oil is chromatographed on silica gel to give 737 mg. (62%) of oil; λmax. 4.77 (azido) and 5.78 μ (carbonyl groups).

Workup

  1. additionThe cooled solution is poured into 300 ml
  2. extractionof water and the resulting mixture is extracted several times with ether
  3. washThe combined ether extracts are washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe residual oil is chromatographed on silica gel
  6. customto give 737 mg

Sources & evidence

ORD record
ord-9a1265adf5e14039a48042be51b6a1d2
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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