Reaktion #422671

Reaktionsgleichung

2-ethynylpyridine

(3aR,5R,6S,7R,7aR)-5-(azidomethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

ethanol

→

title compound

Ausbeute 25.5%

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yl-1H-1,2,3-triazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

Ausbeute 25.5%

Lösungsmittel

H2O

2-methylpropan-2-ol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 5 mL seal vial
2. 2
   Sonstigeequipped with a stir bar
3. 3
   SonstigeThe vial was evacuated
4. 4
   workup.ADDITIONfilled with N2
5. 5
   workup.ADDITIONwas added into the mixture
6. 6
   workup.ADDITIONwas added into the mixture
7. 7
   Sonstigedried via lyophilization
8. 8
   SonstigeThe mixture was purified with Yamazen C1 acidic condition

Vorschrift

In a 5 mL seal vial equipped with a stir bar, a septum was added (3aR,5R,6S,7R,7aR)-5-(azidomethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (40.00 mg; 0.15 mmol; 1.00 eq.), copper Not supported by ACD (65.10 mg; 1.02 mmol; 7.00 eq.) and copper (2+) sulfate pentahydrate (7.31 mg; 0.03 mmol; 0.20 eq.). The vial was evacuated and filled with N2. This procedure was repeated for twice before ethanol (0.40 ml)/water (0.60 ml)/2-methylpropan-2-ol (1.00 ml) and 2-ethynylpyridine (0.03 ml; 0.29 mmol; 2.00 eq.) was added into the mixture. The mixture was stirred at room temperature for overnight before 3 mL H2O was added into the mixture and dried via lyophilization. The mixture was purified with Yamazen C1 acidic condition affording 14.4 mg (20.1%) of the title compound as a white solid (HPLC 99%, retention time=1.73 min) once lyophilized.

Quelle