Реакция #1702096

Уравнение реакции

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

Выход 80.5%

Растворители

EtOAc

pyridine

Условия реакции

Обработка

1. 1
   Температураthe heat to the oil bath
2. 2
   workup.STIRRINGto stir for a further 9 hours
3. 3
   Экстракцияextracted with H2O
4. 4
   ЭкстракцияThe organic phase was then extracted with brine
5. 5
   Сушкаdried over Na2SO4
6. 6
   ДругоеThe drying agent was removed by vacuum filtration
7. 7
   Концентрированиеthe filtrate was concentrated

Методика

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.

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