Sodium Azide → HCID 19365021, compound

HRID 850716Notes

Reaction equation

HRID 850716 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH:15]2[CH:10]([CH:11]=[CH:12][CH2:13][CH:14]2[CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH:15]2[CH:10]([CH:11]=[CH:12][CH2:13][CH:14]2[CH2:17][N:29]=[N+:30]=[N-:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19364987HCID 19364987, compound

Product 1

HCID 19365021HCID 19365021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 33 g (0.08 mol) of (1RS,2RS,6RS)-8-tert-butyloxycarbonyl-2-(4-toluenesulphonyloxymethyl)-8-azabicyclo[4.3.0]non-4-ene (title compound from Example K.5.) and 15.8 g (0.24 mol) of sodium azide in 200 ml of N,N-dimethylformamide is stirred at 70° C. for 40 h. After cooling, the solution is diluted with water (500 ml) and extracted three times with 250 ml of petroleum ether on each occasion. The combined organic phase is washed with 5% strength sodium hydrogen carbonate solution, dried (sodium sulphate) and concentrated.

Sources & evidence

ORD record
ord-5a43c060f31f489eb679d99bb60b0a26
Source dataset
uspto-grants-2000_01
Patent number
US06018054

Reaction notes

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