Reaktion #539761

ord-03188c9002a54bd28af27494fb8f517b

Reaktionsgleichung

CS(=O)(=O)OCC1(COS(C)(=O)=O)O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)[C@@H](I)[C@@H]1OCc1ccccc1
Compound 87
CS(=O)(=O)OCC1(COS(C)(=O)=O)O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)[C@@H](I)[C@@H]1OCc1ccccc1
9-(3-O-Benzyl-2-deoxy-2-iodo-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-threo-pentofuranosyl)-6-N-benzoyladenine
[N-]=[N+]=[N-].[Na+]
sodium azide
[N-]=[N+]=[N-]
azide
→
CS(=O)(=O)OCC1(COS(C)(=O)=O)O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)[C@H](N=[N+]=[N-])[C@@H]1OCc1ccccc1
9-(2-azido-3-O-Benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine

Edukte

CS(=O)(=O)OCC1(COS(C)(=O)=O)O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)[C@@H](I)[C@@H]1OCc1ccccc1
Compound 87
CS(=O)(=O)OCC1(COS(C)(=O)=O)O[C@@H](n2cnc3c(NC(=O)c4ccccc4)ncnc32)[C@@H](I)[C@@H]1OCc1ccccc1
9-(3-O-Benzyl-2-deoxy-2-iodo-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-threo-pentofuranosyl)-6-N-benzoyladenine
[N-]=[N+]=[N-].[Na+]
sodium azide
[N-]=[N+]=[N-]
azide

Reagenzien

Keine

Lösungsmittel

CN(C)C=O.O
DMF water

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Compound 87 (30 mg) was dissolved in DMF/water 1:1 (2 ml) and followed by sodium azide (26 mg, 10 equiv.). The reaction mixture stirred at 80° C. overnight. LCMS confirms conversion of starting material to product substituted with azide.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08492390B2uspto-grants-2013_07