反应 #7407

反应方程式

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

piperidine

→

title compound

收率 82.0%

6-Chloro-N-{(3S)-1-[(1R)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

收率 82.0%

溶剂

DCM

triethylamine

反应条件

后处理

1. 1
   浓缩The mixture was then concentrated under reduced pressure
2. 2
   其他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
   其他The reaction mixture was partitioned between DCM and water
7. 7
   萃取The organic extract
8. 8
   浓缩was concentrated under reduced pressure
9. 9
   其他the residue purified
10. 10
    洗涤SPE (silica, eluting with cyclohexane:ethyl acetate 5:1, 3:1, 1:1, 1:3 and ethyl acetate)

实验过程

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 (3 ml) was treated with trifluoroacetic acid (3 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, piperidine (0.007 ml) 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 (0.021 g) as a colourless gum.

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