Sodium Azide → HCID 86592849, compound

HRID 2212189Notes

Reaction equation

HRID 2212189 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH:16]([CH2:18]OS(C)(=O)=O)[CH2:15][CH:14]([N:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:34])[C:28]=3[C:27]3=[N:35][O:36][C:37]([CH3:38])=[C:26]3[C:25]2=[O:39])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:13][CH:14]([N:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:34])[C:28]=3[C:27]3=[N:35][O:36][C:37]([CH3:38])=[C:26]3[C:25]2=[O:39])[CH2:15][CH:16]([CH2:18][N:1]=[N+:2]=[N-:3])[CH2:17]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86592848HCID 86592848, compound

Product 1

HCID 86592849HCID 86592849, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Add NaN3 (0.33 g, 5.1 mmol) to a solution of 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-5-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.87 g, 1.7 mmol) in DMF (20 mL). Heat 24 H at 60° C., cool to 0° C. and quench with water. Concentrate to dryness. Partition between 20% iPrOH/CHCl3 and water. Extract 3×CHCl3. Wash the combined organics 2× with brine, dry over Na2SO4, filter and concentrate to dryness to afford the title compound (0.67 g, 84%) as a white foam as a mixture of cis isomers. MS(IS) 473.2 (M+); TLC (50% EtOAc/hexanes) Rf=0.8.

Workup

  1. temperaturecool to 0° C.
  2. customquench with water
  3. concentrationConcentrate to dryness
  4. customPartition between 20% iPrOH/CHCl3 and water
  5. extractionExtract 3×CHCl3
  6. washWash the combined organics 2× with brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-aeeee895e262419aad5093190cc8aa68
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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