2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → 1-(2-iodoacetamido)-N-((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-yl)-3,6,9,12-tetraoxapentadecan-15-amide

HRID 1057085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057085
C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[NH2:19][C@@H:20]([CH:74]([CH3:76])[CH3:75])[C:21]([NH:23][C@@H:24]([CH3:73])[C:25]([NH:27][CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH2:32][C@H:33]2[CH:39]=[N:38][C:37]3[CH:40]=[C:41]([O:46][CH2:47][CH2:48][CH2:49][O:50][C:51]4[C:52]([O:69][CH3:70])=[CH:53][C:54]5[C:60](=[O:61])[N:59]6[CH:62]=[C:63](/[CH:65]=[CH:66]/[CH3:67])[CH2:64][C@H:58]6[CH:57]=[N:56][C:55]=5[CH:68]=4)[C:42]([O:44][CH3:45])=[CH:43][C:36]=3[C:35](=[O:71])[N:34]2[CH:72]=1)=[O:26])=[O:22].[I:77][CH2:78][C:79](=[O:98])[NH:80][CH2:81][CH2:82][O:83][CH2:84][CH2:85][O:86][CH2:87][CH2:88][O:89][CH2:90][CH2:91][O:92][CH2:93][CH2:94][C:95](O)=[O:96]>ClCCl>[I:77][CH2:78][C:79]([NH:80][CH2:81][CH2:82][O:83][CH2:84][CH2:85][O:86][CH2:87][CH2:88][O:89][CH2:90][CH2:91][O:92][CH2:93][CH2:94][C:95]([NH:19][C@@H:20]([CH:74]([CH3:76])[CH3:75])[C:21]([NH:23][C@@H:24]([CH3:73])[C:25]([NH:27][CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH2:32][C@H:33]2[CH:39]=[N:38][C:37]3[CH:40]=[C:41]([O:46][CH2:47][CH2:48][CH2:49][O:50][C:51]4[C:52]([O:69][CH3:70])=[CH:53][C:54]5[C:60](=[O:61])[N:59]6[CH:62]=[C:63](/[CH:65]=[CH:66]/[CH3:67])[CH2:64][C@H:58]6[CH:57]=[N:56][C:55]=5[CH:68]=4)[C:42]([O:44][CH3:45])=[CH:43][C:36]=3[C:35](=[O:71])[N:34]2[CH:72]=1)=[O:26])=[O:22])=[O:96])=[O:98]

Komponenten

5

Edukt 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 872435891-Iodo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acidHCID 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

Produkt 1

HCID 904080301-(2-iodoacetamido)-N-((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-yl)-3,6,9,12-tetraoxapentadecan-15-amideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.007 g, 0.0290 mmol, 1.0 eq) was added to a solution of amine 20c (assumed 100%, 0.023 g, 0.0290 mmol, 1.0 eq) and 1-iodo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acid (I5)(0.0126 g, 0.0290 mmol, 1.0 eq) in dry dichloromethane (2 mL). The reaction mixture was stirred for 18 hours, then diluted with DCM (6 mL) and washed with water (2×10 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was subjected to flash chromatography (silica gel; 40:1 v/v DCM/MeOH to 5:1 v/v DCM/MeOH) to afford the product as a pale yellow oil (0.0043 g, 29%). LC/MS (2.380 min (ES+)), m/z: 605.0 ½[M+2H]+.

Aufarbeitung

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-373c80d943914826bc966ae19280a5cd
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399073B2

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