2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate → HCID 90411542, Verbindung

HRID 1427736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427736
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][C:10]([O:12]N1C(=O)CCC1=O)=O.[NH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:85]=[CH:84][C:38]([C:39]([C:41]2[CH:83]=[CH:82][C:44]([O:45][CH2:46][CH2:47][CH2:48][NH:49][C:50](=[O:81])[CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][NH:65][C:66](=[O:80])[CH2:67][CH2:68][CH2:69][CH2:70][CH:71]3[CH:78]4[CH:74]([NH:75][C:76](=[O:79])[NH:77]4)[CH2:73][S:72]3)=[CH:43][CH:42]=2)=[O:40])=[CH:37][CH:36]=1>C(Cl)Cl>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH2:8][CH2:9][C:10](=[O:12])[NH:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]1[CH:36]=[CH:37][C:38]([C:39]([C:41]2[CH:83]=[CH:82][C:44]([O:45][CH2:46][CH2:47][CH2:48][NH:49][C:50](=[O:81])[CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][NH:65][C:66](=[O:80])[CH2:67][CH2:68][CH2:69][CH2:70][CH:71]3[CH:78]4[CH:74]([NH:75][C:76](=[O:79])[NH:77]4)[CH2:73][S:72]3)=[CH:43][CH:42]=2)=[O:40])=[CH:84][CH:85]=1

Komponenten

4

Edukt 2

HCID 46205972,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoateHCID 90411535HCID 90411535, Verbindung

Produkt 1

HCID 90411542HCID 90411542, VerbindungAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate (0.65 g, 2.43 mmol) was added to a solution of crude N-(3-(4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)amino)-benzoyl)phenoxy)propyl)-1-(5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide (2 g, 2.11 mmol) in DCM (20 mL) and the reaction mixture was stirred for 2 hs at room temperature. Upon completion, reaction was then concentrated under reduced pressure, and purified by silica gel chromatography (DCM to DCM:MeOH, gradient) to yield 1.70 g (1.55 mmol, 73%) N-(3-(4-(4-((17-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-15-oxo-4,7,10-trioxa-14-azaheptadecyl)-amino)benzoyl)phenoxy)propyl)-1-(5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide as yellow oil.

Aufarbeitung

  1. customUpon completion, reaction
  2. concentrationwas then concentrated under reduced pressure
  3. custompurified by silica gel chromatography (DCM to DCM:MeOH, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a37d2ce55aae448fbc6a971df0fc2fe5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933261B2

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