Hydrochloric Acid → (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid

HRID 388655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388655
C[O:2][C:3]([C@@:5]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[C@@H:8]([CH2:9][C@H:10]([O:26][C:27]3[C:36]4[C:31](=[C:32]([CH3:39])[C:33]([O:37][CH3:38])=[CH:34][CH:35]=4)[N:30]=[C:29]([C:40]4[S:41][CH:42]=[C:43]([C:45]#[CH:46])[N:44]=4)[CH:28]=3)[CH2:11][CH2:12]1)[C:7](=[O:47])[NH:6]2)=[O:4].[Li+].[OH-].Cl>O1CCCC1.O>[C:45]([C:43]1[N:44]=[C:40]([C:29]2[CH:28]=[C:27]([O:26][C@H:10]3[CH2:9][C@@H:8]4[N:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C@H:22]5[C@:5]([C:3]([OH:4])=[O:2])([NH:6][C:7]4=[O:47])[CH2:23]5)[CH2:12][CH2:11]3)[C:36]3[C:31](=[C:32]([CH3:39])[C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[N:30]=2)[S:41][CH:42]=1)#[CH:46]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 87472167(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester

Produkt 1

HCID 87472044(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of compound 37 (0.11 g, 1 eq.) and LiOH (0.022 g, 5 eq.) in a mixture of tetrahydrofuran (5 mL) and water (5 mL) was stirred at room temperature overnight. HCl (1N) was added and the mixture was extracted with dichloromethane. Dried organics were evaporated in vacuo. The crude residue was purified by chromatography on silica gel to give compound 38 in 46% yield. MS (ESI, EI+) m/z=644 (MH+).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. customDried organics were evaporated in vacuo
  3. customThe crude residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c7ba6fde23a54dad91b6694836b4561d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377962B2

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