Reaktion #68095

Reaktionsgleichung

2-aminoethanol

diisopropyl ether

1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

2-aminoethanol

2-aminoethanol

ethyl chlorocarbonate

→

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((2-hydroxyethyl)amino)carbonyl)-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Lösungsmittel

diethyl ether

triethylamine

tetrahydrofuran

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   Temperaturcooling
3. 3
   workup.STIRRINGAfter stirred at the same temperature for 3 hours
4. 4
   workup.STIRRINGstirred for 1.5 hours
5. 5
   workup.STIRRINGstirred at room temperature for 40 min
6. 6
   Sonstigethe organic layer was separated
7. 7
   Extraktionthe aqueous layer was extracted with ethyl acetate
8. 8
   Waschenwashed sequentially with water and aqueous saturated sodium chloride solution
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was removed under reduced pressure
11. 11
    SonstigeTo the residue thus obtained
12. 12
    Filtrationthe resulting solid was filtered

Vorschrift

To 3.0 mL of tetrahydrofuran suspension containing 0.15 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid, 39 μL of triethylamine was added at room temperature, 25 μL of ethyl chlorocarbonate was added dropwise under ice-cooling, and the reaction mixture was stirred at the same temperature for 2 hours. Then, 15 μL of 2-aminoethanol was added dropwise. After stirred at the same temperature for 3 hours, 15 μL of 2-aminoethanol was added dropwise and stirred for 1.5 hours. Further, 15 μL of 2-aminoethanol was added dropwise and stirred at room temperature for 40 min. To the reaction mixture, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, diethyl ether and diisopropyl ether were added, and the resulting solid was filtered to give 84 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((2-hydroxyethyl)amino)carbonyl)-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a slight yellow solid.

Quelle