Реакция #7414

Уравнение реакции

(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

HOBT

benzyl (3S)-piperidin-3-ylcarbamate

→

title compound

Выход 42.5%

Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate

Выход 42.5%

Растворители

DCM

triethylamine

DCM

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 h
3. 3
   ДругоеThe mixture was partitioned between DCM and water
4. 4
   ПромывкаThe separated organic extracts were washed with water and brine
5. 5
   Сушкаdried (over magnesium sulphate)
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was purified
8. 8
   ПромывкаBiotage™ chromatography (eluting with hexane:ethyl acetate 1:7→1:10)

Методика

A solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.408 g) in DCM (21 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.394 g), HOBT (0.278 g) and triethylamine (0.286 ml) and stirred at room temperature for 1 h. A solution of benzyl (3S)-piperidin-3-ylcarbamate (0.361 g) in DCM (1 ml) was then added and stirring continued for 72 h. The mixture was partitioned between DCM and water. The separated organic extracts were washed with water and brine, dried (over magnesium sulphate), and concentrated under reduced pressure. The residue was purified using Biotage™ chromatography (eluting with hexane:ethyl acetate 1:7→1:10) to give the title compound (0.268 g) as an oil.

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