Hydrochloric Acid → HCID 68008759, Verbindung

HRID 1429094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429094
[NH2:1][C@@H:2]1[C:16](=[O:17])[N:15]2[CH2:18][C@H:19]([O:21][C:22]3[N:23]=[C:24]4[C:29](=[C:30]5[C:35]=3[CH:34]=[CH:33][CH:32]=[CH:31]5)[CH:28]=[CH:27][CH:26]=[CH:25]4)[CH2:20][C@H:14]2[C:13](=[O:36])[NH:12][C@:11]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:37][C@H:10]2[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH3:44][C:45]1[O:49][N:48]=[C:47]([C:50](O)=[O:51])[CH:46]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:44][C:45]1[O:49][N:48]=[C:47]([C:50]([NH:1][C@@H:2]2[C:16](=[O:17])[N:15]3[CH2:18][C@H:19]([O:21][C:22]4[N:23]=[C:24]5[C:29](=[C:30]6[C:35]=4[CH:34]=[CH:33][CH:32]=[CH:31]6)[CH:28]=[CH:27][CH:26]=[CH:25]5)[CH2:20][C@H:14]3[C:13](=[O:36])[NH:12][C@:11]3([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:37][C@H:10]3[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:51])[CH:46]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 68008345HCID 68008345, Verbindung

Produkt 1

HCID 68008759HCID 68008759, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-amino-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate, Hydrochloric Acid (Example 18b, 5.00 g, 8.24 mmol), 5-methylisoxazole-3-carboxylic acid (1.15 g, 9.06 mmol) and 2-(3H41,2,31triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (3.44 g, 9.06 mmol) in dichloromethane (82 ml) was added N-ethyl-N-isopropylpropan-2-amine (5.03 ml, 28.8 mmol). The mixture was stirred at rt for 2 h, and then quenched with saturated aqueous sodium carbonate solution. The organic layer was washed with 1N HCl, separated, filtered, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to provide a white foam. This material was purified flash chromatography on silica gel (4:1 dichloromethane/ethyl acetate) to give (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (4.5 g, 80% yield).

Aufarbeitung

  1. customquenched with saturated aqueous sodium carbonate solution
  2. washThe organic layer was washed with 1N HCl
  3. customseparated
  4. filtrationfiltered
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto provide a white foam
  8. customThis material was purified flash chromatography on silica gel (4:1 dichloromethane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0ad81805356149f6a5a1c18871d7f4e2
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937041B2

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