반응 #7407

반응 방정식

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

수율 82.0%

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

수율 82.0%

용매

DCM

triethylamine

반응 조건

후처리

1. 1
   농축The mixture was then concentrated under reduced pressure
2. 2
   기타to 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
   기타The reaction mixture was partitioned between DCM and water
7. 7
   추출The organic extract
8. 8
   농축was concentrated under reduced pressure
9. 9
   기타the residue purified
10. 10
    세척SPE (silica, eluting with cyclohexane:ethyl acetate 5:1, 3:1, 1:1, 1:3 and ethyl acetate)

실험 절차

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.

출처