Methanol → (S)-2-amino-N1-((S)-1,1-diethoxypropan-2-yl)-N1-(quinolin-8-ylmethyl)-N4-tritylsuccinamide

HRID 718931

Reaktionsgleichung

Reaktionsgleichung von HRID 718931
[CH2:1]([O:3][CH:4]([O:63][CH2:64][CH3:65])[C@@H:5]([N:7]([CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[C:57]2[C:62]=1[N:61]=[CH:60][CH:59]=[CH:58]2)[C:8](=[O:51])[C@@H:9]([NH:33]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:10][C:11](=[O:32])[NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:6])[CH3:2].N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:33][C@@H:9]([CH2:10][C:11]([NH:12][C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:32])[C:8]([N:7]([C@@H:5]([CH3:6])[CH:4]([O:3][CH2:1][CH3:2])[O:63][CH2:64][CH3:65])[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[C:57]2[C:62]=1[N:61]=[CH:60][CH:59]=[CH:58]2)=[O:51]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 86698535(9H-Fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate

Produkt 1

HCID 67075012(S)-2-amino-N1-((S)-1,1-diethoxypropan-2-yl)-N1-(quinolin-8-ylmethyl)-N4-tritylsuccinamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

(9H-Fluoren-9-yl)methyl (S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate (Compound III-20) 23.4 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 15.3 g, (yield 88%).

Aufarbeitung

  1. washwashed with water (150 ml×3)
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel with PE

Quellen und Nachweise

ORD-Eintrag
ord-8b5b6e43b39047718b41cf43824e1e64
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193734B2

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