تفاعل #2195880

معادلة التفاعل

1H-Benzotriazolium

dimethylamine

methyl N-{(1R)-1-(2,4-difluorophenyl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate

1,1′-thiocarbonyldiimidazole

→

methyl N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate

المردود 58.5%

المذيبات

tetrahydrofuran

dichloromethane

Water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred for a further 18 hours
2. 2
   غسيلeluting with a gradient (8:1 to 1:2 cyclohexane:ethyl acetate)
3. 3
   أخرىevaporated

الإجراء التجريبي

A solution of methyl N-{(1R)-1-(2,4-difluorophenyl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate (203 mg) and 1,1′-thiocarbonyldiimidazole (100 mg) in dichloromethane (5 ml) was left to stand for 18 hours. Water (10□1) was added to the reaction mixture and this was then stirred rapidly for 30 minutes. After this, 1H-Benzotriazolium, 1-[bis(dimethylamino)methylene]-, tetrafluoroborate(1-), 3-oxide (TBTU, 321 mg) and a solution of dimethylamine in tetrahydrofuran (0.5 ml of 2M solution) were added. The reaction mixture was stirred for a further 18 hours and was then passed down an SPE (5 g, silica) eluting with a gradient (8:1 to 1:2 cyclohexane:ethyl acetate). The required fractions were combined and evaporated to furnish methyl N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate (100 mg).

المصدر