Piperidine → (S)-2-amino-N-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-yl)-3-methylbutanamide

HRID 1057083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057083
N1CCCCC1.[CH3:7][O:8][C:9]1[C:56]([O:57][CH2:58][CH2:59][CH2:60][O:61][C:62]2[C:63]([O:80][CH3:81])=[CH:64][C:65]3[C:71](=[O:72])[N:70]4[CH:73]=[C:74](/[CH:76]=[CH:77]/[CH3:78])[CH2:75][C@H:69]4[CH:68]=[N:67][C:66]=3[CH:79]=2)=[CH:55][C:12]2[N:13]=[CH:14][C@@H:15]3[CH2:21][C:20](/[CH:22]=[CH:23]/[CH2:24][NH:25][C:26](=[O:54])[C@@H:27]([NH:29][C:30](=[O:53])[C@@H:31]([NH:35]C(=O)OCC4C5C=CC=CC=5C5C4=CC=CC=5)[CH:32]([CH3:34])[CH3:33])[CH3:28])=[CH:19][N:16]3[C:17](=[O:18])[C:11]=2[CH:10]=1>CN(C=O)C.C(Cl)Cl>[NH2:35][C@@H:31]([CH:32]([CH3:34])[CH3:33])[C:30]([NH:29][C@@H:27]([CH3:28])[C:26]([NH:25][CH2:24]/[CH:23]=[CH:22]/[C:20]1[CH2:21][C@H:15]2[CH:14]=[N:13][C:12]3[CH:55]=[C:56]([O:57][CH2:58][CH2:59][CH2:60][O:61][C:62]4[C:63]([O:80][CH3:81])=[CH:64][C:65]5[C:71](=[O:72])[N:70]6[CH:73]=[C:74](/[CH:76]=[CH:77]/[CH3:78])[CH2:75][C@H:69]6[CH:68]=[N:67][C:66]=5[CH:79]=4)[C:9]([O:8][CH3:7])=[CH:10][C:11]=3[C:17](=[O:18])[N:16]2[CH:19]=1)=[O:54])=[O:53]

Komponenten

5

Edukt 2

HCID 8082PiperidineHCID 131736462(9H-fluoren-9-yl)methyl(S)-1-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-ylamino)-3-methyl-1-oxobutan-2-ylcarbamate

Produkt 1

HCID 90408320(S)-2-amino-N-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-yl)-3-methylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Piperidine (0.04 mL, 4.1 mmol, 13.7 eq.) was added to a stirring mixture of Fmoc amine 19c (0.030 g, 0.0295 mmol, 1 eq.) in anhydrous DMF (0.5 mL) and the mixture was stirred at ambient temperature. After 20 minutes, LCMS showed reaction was completed so the reaction mixture was diluted with DCM (75 mL) and washed with water (3×75 mL). The organic layer was dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Co-evaporation with n-hexanes afforded the product as a brown oil, and the material was not subjected to further purification (0.023 g, assumed 100%). LC/MS (1.868 min (ES+)), m/z: 794.2 [M+H]+.

Aufarbeitung

  1. customreaction
  2. washwashed with water (3×75 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customCo-evaporation with n-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d472e6fb29744b64ac061218baf5c704
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399073B2

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