تفاعل #7385

معادلة التفاعل

(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

المردود 42.5%

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

المردود 42.5%

المذيبات

DCM

triethylamine

DCM

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر