N,N-Dimethylethylenediamine → (1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(5-methylpyrazine-2-carboxamido)non-8-enoyl)-4-(phenanthridin-6-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

HRID 1966504

Reaktionsgleichung

Reaktionsgleichung von HRID 1966504
[CH:1]1[C:14]2[C:5](=[N:6][C:7]([O:15][C@H:16]3[CH2:20][NH:19][C@H:18]([C:21]([NH:23][C@:24]4([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:26][C@H:25]4[CH:27]=[CH2:28])=[O:22])[CH2:17]3)=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH3:34][C:35]1[N:36]=[CH:37][C:38]([C:41]([NH:43][C@@H:44]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH:53]=[CH2:54])[C:45](O)=[O:46])=[O:42])=[N:39][CH:40]=1.ON1C(=O)C2C(C3CC2C=C3)C1=O.Cl.CN(C)CCCN=C=NCC.CN(C)CCN>CN(C=O)C>[CH3:34][C:35]1[N:36]=[CH:37][C:38]([C:41]([NH:43][C@@H:44]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH:53]=[CH2:54])[C:45]([N:19]2[CH2:20][C@H:16]([O:15][C:7]3[N:6]=[C:5]4[C:14](=[C:13]5[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]5)[CH:1]=[CH:2][CH:3]=[CH:4]4)[CH2:17][C@H:18]2[C:21]([NH:23][C@:24]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:26][C@H:25]2[CH:27]=[CH2:28])=[O:22])=[O:46])=[O:42])=[N:39][CH:40]=1

Komponenten

7

Edukt 5

HCID 66053N,N-DimethylethylenediamineHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67296752(S)-2-(5-methylpyrazine-2-carboxamido)non-8-enoic acidHCID 86660472(1R,2S)-ethyl 1-((2S,4R)-4-(phenanthridin-6-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

Produkt 1

HCID 86660471(1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(5-methylpyrazine-2-carboxamido)non-8-enoyl)-4-(phenanthridin-6-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(1R,2S)-ethyl 1-((2S,4R)-4-(phenanthridin-6-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate, the title compound of Example 49a, N-hydroxy-5-norbornene-2,3-dicarboximide, and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride can be mixed and stirred in DMF, followed by addition of N,N-dimethylethylene diamine. The reaction produces (1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(5-methylpyrazine-2-carboxamido)non-8-enoyl)-4-(phenanthridin-6-yloxy)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate, which can be dissolved in isopropyl acetate and extracted with aqueous H3PO4, and then extracted with aqueous K2HPO4. The product can be reacted with di-tert-butyldicarbonate in the presence of dimethylaminopyridine, followed by extraction with a mixture of a citric acid solution and a sodium chloride solution, to produce the title compound of Example 49b.

Quellen und Nachweise

ORD-Eintrag
ord-785238ebb21741ffb4aea80c70a27d61
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420596B2

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