Ethanol → HCID 178463401, Verbindung

HRID 335501

Reaktionsgleichung

Reaktionsgleichung von HRID 335501
[N:1]([CH2:4][C@H:5]1[O:13][C@H:12]2[C@H:8]([N:9]=[C:10]([NH:14][CH2:15][CH3:16])[S:11]2)[C@@H:7]([OH:17])[C@@H:6]1[OH:18])=[N+:2]=[N-:3].C(O)C.CC(O)(C)C.[C:27]1([C:33]([OH:37])([C:35]#[CH:36])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.[Cu].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:15]([NH:14][C:10]1[S:11][CH:12]2[O:13][CH:5]([CH2:4][N:1]3[CH:36]=[C:35]([C:33]([OH:37])([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:34])[N:3]=[N:2]3)[CH:6]([OH:18])[CH:7]([OH:17])[CH:8]2[N:9]=1)[CH3:16]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 6386tert-ButanolHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 66550531HCID 66550531, Verbindung

Produkt 1

HCID 178463401HCID 178463401, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 24463Copper sulfate pentahydrateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

In a 10 mL rb flask 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 mg, 0.15 mmol, 1.00 eq.), copper turnings (66 mg; 1.05 mmol; 7.00 eq.) and copper(II)sulfate pentahydrate (7.5 mg; 0.03 mmol; 0.20 eq.). The flask was evacuated and filled with nitrogen. This procedure was repeated twice before ethanol (0.5 ml)/water (0.7 ml)/2-methylpropan-2-ol (1.3 ml) and 2-phenylbut-3-yn-2-ol (22 mg; 0.45 mmol; 3.00 eq.) was added into the mixture and stirred for 24 h to get the reaction completed. Product formation was confirmed by LCMS. The solution was diluted with 2 mL H2O, dried and separated with mass based prep HPLC to afford the desired product.

Aufarbeitung

  1. customThe flask was evacuated
  2. additionfilled with nitrogen
  3. additionwas added into the mixture
  4. customto get the reaction
  5. customdried
  6. customseparated with mass

Quellen und Nachweise

ORD-Eintrag
ord-1ca6b8f8ea5c4d049edeed19d56a9674
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884023B2

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