Potassium Carbonate → Potassium 5-(4'-{[5-({1-[({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethoxy}-carbonyl)-2-butyl-4-chloro-1H-imidazol-1-yl]methyl}biphenyl-2-yl)tetrazol-1-ide

HRID 1361906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361906
C(=O)([O-])[O-].[K+:5].[K+].[CH2:7]([C:11]1[N:12]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[C:53]3[NH:57][N:56]=[N:55][N:54]=3)=[CH:43][CH:42]=2)[C:13]([C:17]([O:19][CH:20]([O:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C@@H:30]([O:36][N+:37]([O-:39])=[O:38])[CH2:31][O:32][N+:33]([O-:35])=[O:34])=[O:24])[CH3:21])=[O:18])=[C:14]([Cl:16])[N:15]=1)[CH2:8][CH2:9][CH3:10]>CC(O)C>[N+:37]([O:36][C@@H:30]([CH2:31][O:32][N+:33]([O-:35])=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:23]([O:22][CH:20]([O:19][C:17]([C:13]1[N:12]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[C:53]3[N-:57][N:56]=[N:55][N:54]=3)=[CH:45][CH:46]=2)[C:11]([CH2:7][CH2:8][CH2:9][CH3:10])=[N:15][C:14]=1[Cl:16])=[O:18])[CH3:21])=[O:24])([O-:39])=[O:38].[K+:5]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 178441694HCID 178441694, Verbindung

Produkt 1

HCID 86622532Potassium 5-(4'-{[5-({1-[({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethoxy}-carbonyl)-2-butyl-4-chloro-1H-imidazol-1-yl]methyl}biphenyl-2-yl)tetrazol-1-ide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Potassium carbonate (945 mg, 6.84 mmol) was added to a stirred solution of 1-[({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate (250 mg, 0.34 mmol) in IPA (6.8 mL). The solution was stirred at 25° C. for 3 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was redissolved in DCM (6 mL). Heptane was added until the compound began to precipitate. The solution was concentrated in vacuo to give the title compound as a white solid. 1H NMR (500 MHz, CD3CN) δ 7.72-7.68 (m, 1H), 7.40-7.33 (m, 2H), 7.33-7.28 (m, 1H), 7.12 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.88-6.82 (m, 1H), 5.47 (s, 2H), 5.32 (ddd, J=13.0, 6.5, 2.5 Hz, 1H), 4.79 (dd, J=13.0, 2.5 Hz, 1H), 4.55 (dd, J=13.0, 6.5 Hz, 1H), 4.08 (td, J=6.5, 3.0 Hz, 2H), 1.71 (q, J=13.0, 7.7 Hz, 2H), 1.61 (hex, J=22.0, 14.5, 7.0 Hz, 4H), 1.50 (d, J=5.5 Hz, 3H) 1.49-1.37 (m, 2H), 1.35-1.26 (m, 2H), 0.85 (t, J=7.5 Hz, 3H); LCMS (M+H) found 731.1.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was redissolved in DCM (6 mL)
  4. additionHeptane was added until the compound
  5. customto precipitate
  6. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d165420ddb1d4af49ab6b4302d7f563a
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880014B2

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