تفاعل #7376

معادلة التفاعل

lithium bis(trimethylsilyl) amide

tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

methyl tosylate

→

title compound

tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىto reach room temperature
2. 2
   أخرىThe mixture was quenched with sodium acetate (0.074 g)
3. 3
   workup.STIRRINGstirred for 1 h
4. 4
   أخرىpartitioned between water and ethyl acetate
5. 5
   غسيلThe separated organic layer was washed with water
6. 6
   تجفيفdried (over magnesium sulphate)
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe residue was purified
9. 9
   غسيلSPE (silica, eluting with cyclohexane:ethyl acetate 10:1, 8:1, 5:1, 3:1, 2:1,1:1)

الإجراء التجريبي

A solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.1 g) in THF (5 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.23 ml), followed by methyl tosylate (0.206 g). The resultant solution was allowed to reach room temperature and stirred for a further 16 h. The mixture was quenched with sodium acetate (0.074 g), stirred for 1 h and partitioned between water and ethyl acetate. The separated organic layer was washed with water, dried (over magnesium sulphate), and concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane:ethyl acetate 10:1, 8:1, 5:1, 3:1, 2:1,1:1) to give the title compound (0.101 g) as a colourless gum.

المصدر