Potassium Carbonate → potassium [2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methyl (5R)-5,6-dinitrooxyhexanoate

HRID 1173002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173002
[N+:1]([O:4][C@@H:5]([CH2:41][O:42][N+:43]([O-:45])=[O:44])[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:32]=[N:33][NH:34][N:35]=3)=[CH:21][CH:20]=2)[C:16]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:15][C:14]=1[Cl:40])=[O:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+:50].[K+]>CC(O)C>[N+:1]([O:4][C@@H:5]([CH2:41][O:42][N+:43]([O-:45])=[O:44])[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:32]=[N:33][N-:34][N:35]=3)=[CH:21][CH:20]=2)[C:16]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:15][C:14]=1[Cl:40])=[O:10])([O-:3])=[O:2].[K+:50]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 24958723HCID 24958723, Verbindung

Produkt 1

HCID 140552336potassium [2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methyl (5R)-5,6-dinitrooxyhexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a mixture of (2-butyl-4-chloro-1-{[2′-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methyl (5R)-5,6-bis(nitrooxy)hexanoate (349.3 mg, 0.543 mmol) and potassium carbonate (922.7 mg, 6.68 mmol) was added 2-propanol (25 mL). After 30 minutes, the reaction mixture was filtered and concentrated in vacuo. More washings of the residual solids were performed with ethyl acetate, and the product was precipitated with hexanes. Repeating the cycle twice and drying of the solid in vacuo afforded the title compound as a white solid. 1H NMR (500 MHz, CD3CN) δ 7.62 (dd, J=1.3, 7.3 Hz, 1H), 7.39 (dt, J=1.6, 7.4 Hz, 1H), 7.36 (dt, J=1.6, 7.3 Hz, 1H), 7.31 (dd, J=1.7, 7.4 Hz, 1H), 7.14 (d, J=8.2 Hz, 2H), 6.83 (d, J=8.2 Hz, 2H), 5.27 (dq, J=2.6, 6.4 Hz, 1H), 5.13 (s, 2H), 4.96 (s, 2H), 4.76 (dd, J=2.6, 12.9 Hz, 1H), 4.51 (dd, J=6.1, 12.9 Hz, 1H), 2.54 (t, J=7.7 Hz, 2H), 2.05 (dt, J=1.8, 7.1 Hz, 2H), 1.48-1.68 (m, 6H), 1.30 (pent, J=7.5 Hz, 2H), 0.85 (t, J=7.3 Hz, 3H). LCMS: m/e 643.2 (M+H).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe product was precipitated with hexanes
  4. customRepeating the cycle twice and drying of the solid in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ad5f1171dcfc4f3eaaec841421705c6d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834042B2

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