Sodium Azide → HCID 15586834, compound

HRID 1982184Notes

Reaction equation

HRID 1982184 reaction equation
[C:1]([O:4][CH:5]1[CH:12]([O:13][C:14](=[O:16])[CH3:15])[CH:11]([O:17][C:18](=[O:20])[CH3:19])[C:10]2([CH2:22]Br)[CH2:21][CH:6]1[NH:7][C:8](=[O:24])[O:9]2)(=[O:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[C:1]([O:4][CH:5]1[CH:12]([O:13][C:14](=[O:16])[CH3:15])[CH:11]([O:17][C:18](=[O:20])[CH3:19])[C:10]2([CH2:22][N:25]=[N+:26]=[N-:27])[CH2:21][CH:6]1[NH:7][C:8](=[O:24])[O:9]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13309815HCID 13309815, compound

Product 1

HCID 15586834HCID 15586834, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7,8-Triacetoxy-1-bromomethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (as described in Example 1 of the Japanese Patent Application No. 144309/1981, pp. 37) (4.1 g) is dissolved in dimethylformamide (15 ml), and sodium azide (1.0 g) is added to the solution, followed by stirring under heating on a bath of the temperature of 130° to 140° C. for 7 hours. The reaction mixture is concentrated under reduced pressure and further freed of the dimethylformamide azeotropically with toluene, under reduced pressure. 20% Aqueous methanol (100 ml) is added to the residue, which is then allowed to stand overnight in a refrigerator. The resultant crystals are recovered by filtration, washed with 20% aqueous methanol cooled with ice, and dried to produce 6,7,8-triacetoxy-1-azidomethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (2.7 g).

Workup

  1. temperatureunder heating on a bath of the temperature of 130° to 140° C. for 7 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. addition20% Aqueous methanol (100 ml) is added to the residue, which
  4. filtrationThe resultant crystals are recovered by filtration
  5. washwashed with 20% aqueous methanol
  6. temperaturecooled with ice
  7. customdried

Sources & evidence

ORD record
ord-3c49d48b9e9441fb885462e76ac4440c
Source dataset
uspto-grants-1986_06
Patent number
US04595678

Reaction notes

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