Reaktion #617867

Reaktionsgleichung

methyl 5-amino-3-methyl-4-(4-methylthiazol-2-yl)thiophene-2-carboxylate

bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic anhydride

→

5-[(3-Carboxy-bicyclo[2.2.2]oct-2-ene-2-carbonyl)-amino]-3-methyl-4-(4-methyl-thiazol-2-yl)-thiophene-2-carboxylic acid methyl ester

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 65° C. overnight
2. 2
   ExtraktionThe reaction mixture was extracted with EtOAc and 1M aqueous HCl
3. 3
   Trocknenthe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe compound was purified by silica gel chromatography
7. 7
   workup.ADDITIONa mixture of CH2Cl2:MeOH (20:1 v/v) as eluant

Vorschrift

To the solution of methyl 5-amino-3-methyl-4-(4-methylthiazol-2-yl)thiophene-2-carboxylate (61 mg, 227 μmol, Int1.2) in CH3CN (7 mL) were added DMAP (55.5 mg, 455 μmol) and bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic anhydride (40.5 mg, 227 μmol, CAS RN 151813-29-5). After stirring at RT for 3 h, the reaction mixture was stirred at 65° C. overnight. The reaction mixture was extracted with EtOAc and 1M aqueous HCl, the organic layer was dried over Na2SO4, filtered and evaporated. The compound was purified by silica gel chromatography using a mixture of CH2Cl2:MeOH (20:1 v/v) as eluant. Brown solid. MS (ESI): m/z=447.1 [M+H]+.

Quelle