تفاعل #7372

معادلة التفاعل

D-alanine tert-butylester

N,N-diisopropylethyamine

ethyl 2-azido-4-bromobutanoate

sodium iodide

→

title compound

المردود 18.9%

tert-Butyl (2R)-2-(3-azido-2-oxopyrrolidin-1-yl)propanoate

المردود 18.9%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated under pressure
2. 2
   أخرىto give a brown oil
3. 3
   أخرىThis oil was partitioned between DCM and water
4. 4
   غسيلThe separated organic layer was washed further with water
5. 5
   تجفيفdried (over magnesium sulphate)
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residual brown oil was purified
8. 8
   غسيلBiotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1)

الإجراء التجريبي

To a solution of D-alanine tert-butylester (1.28 g) and N,N-diisopropylethyamine (1.22 ml) in acetonitrile (15 ml), was added a solution of ethyl 2-azido-4-bromobutanoate (1 g) and sodium iodide (0.02 g) in acetonitrile (5 ml). The mixture was heated at 60° C. for 60 h and then concentrated under pressure to give a brown oil. This oil was partitioned between DCM and water. The separated organic layer was washed further with water and dried (over magnesium sulphate), and concentrated under reduced pressure. The residual brown oil was purified using Biotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1) to give the title compound (0.204 g) as a mixture of two diastereoisomers.

المصدر