反応 #7401

反応方程式

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

trifluoroacetic acid

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

HOBT

N-piperidin-3-ylbenzamide

→

title compound

収率 37.3%

N-{1-[(2R)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-yl}benzamide

収率 37.3%

溶媒

DCM

triethylamine

反応条件

後処理

1. 1
   濃縮The mixture was then concentrated under reduced pressure
2. 2
   その他to give an oil which
3. 3
   workup.STIRRINGAfter stirring at room temperature for 1 h
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 48 h
6. 6
   その他The reaction mixture was partitioned between DCM and water
7. 7
   抽出The organic extract
8. 8
   濃縮was concentrated under reduced pressure
9. 9
   その他the residue purified
10. 10
    洗浄SPE (silica, eluting with cyclohexane:ethyl acetate 5:1, 3:1, 1:1, 1:3 and ethyl acetate)

実験手順

A solution of tert-butyl (2R)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino)-2-oxopyrrolidin-1-yl)propanoate (0.025 g) in DCM (1 ml) was treated with trifluoroacetic acid (1 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.013 g), HOBT (0.009 g) and triethylamine (0.023 ml). After stirring at room temperature for 1 h, N-piperidin-3-ylbenzamide (0.015 g) was added and stirring was continued for 48 h. The reaction mixture was partitioned between DCM and water. The organic extract was concentrated under reduced pressure and the residue purified using SPE (silica, eluting with cyclohexane:ethyl acetate 5:1, 3:1, 1:1, 1:3 and ethyl acetate) to give the title compound (0.012 g) as a colourless gum.

出典