Sodium Azide → HCID 86607079, compound

HRID 602337Notes

Reaction equation

HRID 602337 reaction equation
CS(O[C@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:8]([C:18](=[O:33])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C:27]3=[O:32])=[CH:22][CH:21]=2)[CH2:7]1)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C)C=O>[N:34]([C@@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[C@@H:8]([C:18](=[O:33])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C:27]3=[O:32])=[CH:22][CH:21]=2)[CH2:7]1)=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58691261HCID 58691261, compound

Product 1

HCID 86607079HCID 86607079, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

9.2 A mixture of 5.4 g (11.7 mmol) of tert-butyl (2R,4R)-4-methanesulfonyloxy-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate and 3.69 g (56.8 mmol) of sodium azide in 50 ml of dimethylformamide (DMF) is stirred at 60° C. for 12 hours. The insoluble matter is subsequently filtered off, and the filtrate is evaporated to dryness under reduced pressure. The residue is then dissolved in 20 ml of water, and the aqueous solution is extracted twice with 10 ml of methylene chloride each time. The combined methylene chloride extracts are finally washed once with 10 ml of saturated sodium chloride solution and dried over sodium sulfate. Removal of the drying agent by filtration and stripping-off of the solvent gives 4.8 g (100%) of tert-butyl (2R,4S)-4-azido-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate as slightly yellow crystals, ESI 431.

Workup

  1. filtrationThe insoluble matter is subsequently filtered off
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. dissolutionThe residue is then dissolved in 20 ml of water
  4. extractionthe aqueous solution is extracted twice with 10 ml of methylene chloride each time
  5. washThe combined methylene chloride extracts are finally washed once with 10 ml of saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the drying agent
  8. filtrationby filtration

Sources & evidence

ORD record
ord-a9acebfb0e6e4307b7101e0a4c91e155
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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