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

HRID 1765666

Reaktionsgleichung

Reaktionsgleichung von HRID 1765666
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]([CH3:31])[C@H:16]1[CH2:20][CH2:19][N:18]([C@H:21]([CH3:29])[C:22](OC(C)(C)C)=[O:23])[C:17]1=[O:30])(=[O:14])=[O:13])[CH:6]=[CH:5]2.FC(F)(F)C(O)=O.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[NH:61]1[CH2:66][CH2:65][CH2:64][CH:63]([NH:67][C:68](=[O:75])[C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH2:62]1>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:9](=[CH:4][CH:3]=1)[CH:8]=[C:7]([S:12]([N:15]([CH3:31])[C@H:16]1[CH2:20][CH2:19][N:18]([C@H:21]([CH3:29])[C:22]([N:61]3[CH2:66][CH2:65][CH2:64][CH:63]([NH:67][C:68](=[O:75])[C:69]4[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=4)[CH2:62]3)=[O:23])[C:17]1=[O:30])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22017045N-(piperidin-3-yl)benzamideHCID 69223244tert-butyl (2R)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate

Produkt 1

HCID 69329753N-[1-((2R)-2-{(3S)-3-[[(6-Chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoyl)piperidin-3-yl]benzamideAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (2R)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.017 g) in DCM (0.5 ml) was treated with trifluoroacetic acid (0.5 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 (0.01 g), HOBT (0.007 g) and triethylamine (0.020 ml). After stirring at room temperature for 1 h, N-piperidin-3-ylbenzamide (0.010 g) was added and stirring was continued for 16 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 3:1, 1:1, 1:3, ethyl acetate) to give the title compound (0.012 g) as a pale yellow gum.

Aufarbeitung

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customto give an oil which
  3. stirringAfter stirring at room temperature for 1 h
  4. stirringstirring
  5. waitwas continued for 16 h
  6. customThe reaction mixture was partitioned between DCM and water
  7. extractionThe organic extract
  8. concentrationwas concentrated under reduced pressure
  9. customthe residue purified
  10. washSPE (silica, eluting with cyclohexane:ethyl acetate 3:1, 1:1, 1:3, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-367f32610bc9403c8249085edcbaacbc
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226929B2

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