Sodium hydride → HCID 20820309, compound

HRID 583950Notes

Reaction equation

HRID 583950 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-diazocine-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 then once more 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, and after 15 min, the ice bath is removed and the mixture is stirred at RT overnight. The mixture is diluted with dichloromethane, water is added, the phases are 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 melting point 180° C.; the mass spectrum shows the molecular peaks MH+ and MNH4+ at 371 and 388 Da, respectively.

Workup

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

Sources & evidence

ORD record
ord-53a5c145d64c4b8ea004804828740818
Source dataset
uspto-grants-2005_08
Patent number
US06924305B2

Reaction notes

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