Sodium Azide → HCID 86751719, compound

HRID 1939710Notes

Reaction equation

HRID 1939710 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:17][O:18][C:19]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[P:20]([OH:23])([OH:22])=[O:21])[CH2:11]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:30]=[N+:31]=[N-:32].[Na+]>>[N:30]([CH2:11][C@@H:10]([O:17][O:18][C:19]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[P:20]([OH:23])([OH:22])=[O:21])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:31]=[N-:32]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 86751720HCID 86751720, compound

Product 1

HCID 86751719HCID 86751719, compoundYield 78%

Conditions

Temperature
105 °C

Procedure

(R)-3-O-Benzyl-2-O-(diisopropyl phosphonomethoxyl)-1-O-(methanesulfonyl)glycerol (15, 9 g, 20.53 mmol) (J. J. Bronson, etc. J. Med. Chem. 1989, 32, 1457) and sodium azide (4 g, 61.58 mmol) were mixed in 40 mL of anhydrous N',N'-dimethylformamide. The resulting mixture was stirred at 105° C. for 5 hours. After the solvent was removed under reduced presuure, the residue was added 100 mL of methylene chloride. The mixture was filtered, and the solid was washed with methylene chloride. The filtrate was evaporated, and the residue was purified by flash chromatography on silica gel (methylene chloride:acetone=10:1 to 3:1) to give 6.15 g (78% yield) of the title compound as an oil.

Workup

  1. customAfter the solvent was removed
  2. additionthe residue was added 100 mL of methylene chloride
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with methylene chloride
  5. customThe filtrate was evaporated
  6. customthe residue was purified by flash chromatography on silica gel (methylene chloride:acetone=10:1 to 3:1)

Sources & evidence

ORD record
ord-c6ecb9d826ba4ea2aeb9f82ca6dddc19
Source dataset
uspto-grants-1997_12
Patent number
US05696263

Reaction notes

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