Reaktion #1702096

Reaktionsgleichung

5-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester

4-methyl-cyclohexanecarbonyl chloride

→

5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

Ausbeute 80.5%

Lösungsmittel

EtOAc

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe heat to the oil bath
2. 2
   workup.STIRRINGto stir for a further 9 hours
3. 3
   Extraktionextracted with H2O
4. 4
   ExtraktionThe organic phase was then extracted with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   SonstigeThe drying agent was removed by vacuum filtration
7. 7
   Einengenthe filtrate was concentrated

Vorschrift

5-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester (233 mg, 0.629 mmol) was dissolved in pyridine (4 mL) and then 4-methyl-cyclohexanecarbonyl chloride (506 mg, 3.15 mmol) was added. The reaction was stirred for 7 hours at 100° C., the heat to the oil bath was shut off and the reaction was allowed to stir for a further 9 hours. The reaction was diluted with EtOAc and extracted with H2O. The organic phase was then extracted with brine and dried over Na2SO4. The drying agent was removed by vacuum filtration and the filtrate was concentrated. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (251 mg, 78%) was isolated from the residue by silica gel column chromatography.

Quelle