反応 #7376

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   その他to reach room temperature
2. 2
   その他The mixture was quenched with sodium acetate (0.074 g)
3. 3
   workup.STIRRINGstirred for 1 h
4. 4
   その他partitioned between water and ethyl acetate
5. 5
   洗浄The separated organic layer was washed with water
6. 6
   乾燥dried (over magnesium sulphate)
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The residue was purified
9. 9
   洗浄SPE (silica, eluting with cyclohexane:ethyl acetate 10:1, 8:1, 5:1, 3:1, 2:1,1:1)

実験手順

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.

出典