Sodium Azide → HCID 86759657, compound

HRID 1815976Notes

Reaction equation

HRID 1815976 reaction equation
[Br:1][CH:2]1[CH2:28][O:27][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH3:15])[N:10]=[CH:9]3)=[C:4]2[CH:3]1O.[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O>[N:30]([CH:3]1[C:4]2[C:5](=[CH:6][CH:7]=[C:8]3[C:12]=2[N:11]([CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:15])[N:10]=[CH:9]3)[O:27][CH2:28][CH:2]1[Br:1])=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86759658HCID 86759658, compound

Product 1

HCID 86759657HCID 86759657, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Step A (0.31 g, 0.67 mmol) and sodium azide (0.65 g, 10 mmol) in dimethylsulfoxide (20 mL) was heated at 80° C. for 3 h, cooled to room temperature, and extracted with ethyl acetate. The combined extracts were dried and concentrated to a residue which was purified by chromatography (silica, 30% ethyl acetate in hexane) to give an oil (0.26 g, 68%): LC/MS (+APCI) m/z 423 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. concentrationconcentrated to a residue which
  5. customwas purified by chromatography (silica, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-32356dd0466143528989336c054cb556
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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