Sodium Azide → (4S)-11-[2-(azidomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246550Notes

Reaction equation

HRID 2246550 reaction equation
Cl[CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C)C=O>[N:34]([CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12)=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2522749711-(4S)-[2-(chloromethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 25261568(4S)-11-[2-(azidomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of Compound 3 (950 mg) and sodium azide (255 mg) in dry N,N-dimethylformamide (10 mL) was heated at 70° C. for 3 hours under argon. The N,N-dimethylformamide was removed from the reaction mixture under vacuum and directly eluted on a silica gel using 2% ethanol in dichloromethane to afford the required product in 83% yield (800 mg).

Workup

  1. customThe N,N-dimethylformamide was removed from the reaction mixture under vacuum
  2. washdirectly eluted on a silica gel using 2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-028cdaa59fb54e87ade83acf61ad8751
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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