Sodium Azide → HCID 14261123, compound

HRID 1199268Notes

Reaction equation

HRID 1199268 reaction equation
Br[C@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@H:3]1[O:8][C:6](=[O:7])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4]1.[N-:19]=[N+:20]=[N-:21].[Na+]>>[N:19]([C@@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@H:3]1[O:8][C:6](=[O:7])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4]1)=[N+:20]=[N-:21]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 11034458HCID 11034458, compound

Product 1

HCID 14261123HCID 14261123, compound

Procedure

42.5 g (0.135 mol) of 5(R)-bromo-6-cyclohexyl-2(S)-isopropyl-4(S)-hexanolide and 35 g (0.54 mol) of NaN3 in 480 ml of N,N'-dimethyl-N,N'-propylene urea (DMPU) are stirred at room temperature for 72 hours and then poured onto 1 liter of ice-cold 0.1N HCl. The mixture is then extracted three times with ether, and the combined organic phases are washed twice with 0.1N HCl and three times with brine and dried with MgSO4. After concentrating the solvent by evaporation, the residue is recrystallised from hexane: m.p. 38.5°-39°.

Workup

  1. extractionThe mixture is then extracted three times with ether
  2. washthe combined organic phases are washed twice with 0.1N HCl and three times with brine
  3. dry with materialdried with MgSO4
  4. concentrationAfter concentrating the solvent
  5. customby evaporation
  6. customthe residue is recrystallised from hexane

Sources & evidence

ORD record
ord-a0654a8e0eb640108841228c72db148a
Source dataset
uspto-grants-1990_02
Patent number
US04898977

Reaction notes

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