Sodium hydride → HCID 20820309, compound

HRID 1838760Notes

Reaction equation

HRID 1838760 reaction equation
[NH:1]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5][CH2:4][CH2:3][C:2]1=[O:10].[H-].[Na+].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CN(C=O)C>[C:18]([O:17][C:15]([CH2:14][N:1]1[C:2](=[O:10])[CH2:3][CH2:4][N:5]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6](=[O:9])[CH2:7][CH2:8]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 79177tert-Butyl bromoacetate2×HCID 575184HCID 575184, compound

Product 1

HCID 20820309HCID 20820309, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 g of perhydro-1,5-diazocin-2,6-dione are suspended in 30 ml of absolute DMF, and 732 mg of sodium hydride (80%) are then added. The mixture is stirred at RT for 15 min and then cooled to 0° C., and 3.76 ml of tert-butyl bromoacetate are then added. The mixture is stirred at 0° C. for 15 min and at RT for 30 min, and is then once again cooled to 0° C., and another 732 mg of sodium hydride (80%) are added. After 15 min, a further 3.76 ml of tert-butyl bromoacetate are added using a pipette, the ice bath is removed after 15 min and the mixture stirred at RT overnight. The mixture is then diluted with dichloromethane, water is added, and the phases are then separated and the organic phase is washed twice with water. The organic phase is dried over MgSO4 and concentrated, and the residue is dried under high vacuum and recrystallized from n-hexane. This gives 2.5 g of the title compound of m.p. 180° C. The mass spectrum shows the molecular peaks MH+ and MNH4+ at 371 and 388 Da.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe mixture is stirred at 0° C. for 15 min and at RT for 30 min
  3. temperatureis then once again cooled to 0° C.
  4. waitAfter 15 min
  5. customthe ice bath is removed after 15 min
  6. stirringthe mixture stirred at RT overnight
  7. additionThe mixture is then diluted with dichloromethane, water
  8. additionis added
  9. customthe phases are then separated
  10. washthe organic phase is washed twice with water
  11. dry with materialThe organic phase is dried over MgSO4
  12. concentrationconcentrated
  13. customthe residue is dried under high vacuum
  14. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-01501605a2b04ce8bb8272ea38b6e5f8
Source dataset
uspto-grants-2004_01
Patent number
US06673786B1

Reaction notes

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