Sodium Azide → HCID 86585985, compound

HRID 1935635Notes

Reaction equation

HRID 1935635 reaction equation
[CH3:1][C:2]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:14]3[CH2:18][C@H:17]([CH2:19]OS(C)(=O)=O)[O:16][C:15]3=[O:25])[CH:11]=2)[N:6]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])([CH3:4])[CH3:3].[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C=O)C>[N:36]([CH2:19][C@@H:17]1[O:16][C:15](=[O:25])[N:14]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]([C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH2:13]3)[CH2:18]1)=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86585984HCID 86585984, compound

Product 1

HCID 86585985HCID 86585985, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the mesylate from Step 6 (10.56 g, 21.0 mmol) and sodium azide (6.8 g, 104.6 mmol) in DMF (100 ml) is heated at 60° for 7 hours. The DMF is evaporated (45°/0.6 mm) and the residue partitioned between ethyl acetate (250 ml) and water (100 ml). The organic layer is washed with water (100 ml) and brine (50 ml), then dried (MgSO4). Evaporation yielded the product (9.0 g, 95%) as a glassy foam: Anal: Calcd. for C24H27N5O4: C, 64.13; H, 6.05; N, 15.58. Found: C, 63.84; H, 6.15; N, 15.23.

Workup

  1. temperatureis heated at 60° for 7 hours
  2. customThe DMF is evaporated (45°/0.6 mm)
  3. customthe residue partitioned between ethyl acetate (250 ml) and water (100 ml)
  4. washThe organic layer is washed with water (100 ml) and brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-5e187088722042f1bbfeefd6e5a2ee34
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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