1-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-ethoxy-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate → HCID 178467378, Verbindung

HRID 889521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889521
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:46]([C:50]([O:52][CH:53]([O:55][C:56]([O:58][CH2:59][CH2:60][CH2:61][C@@H:62]([O:69][N+:70]([O-:72])=[O:71])[C@H:63]([O:65][N+:66]([O-:68])=[O:67])[CH3:64])=[O:57])[CH3:54])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]>CO>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[C:7]2[C:46]([C:50]([O:52][CH:53]([O:55][C:56]([O:58][CH2:59][CH2:60][CH2:61][C@@H:62]([O:69][N+:70]([O-:72])=[O:71])[C@H:63]([O:65][N+:66]([O-:68])=[O:67])[CH3:64])=[O:57])[CH3:54])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]

Komponenten

3

Edukt 1

HCID 866470171-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-ethoxy-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

Produkt 1

HCID 178467378HCID 178467378, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A methanol (30 mL) suspension of 1-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-ethoxy-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate (2.47 g, 2.53 mmol) was heated to 70° C. for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography on silica gel, eluting with 3-9% methanol/dichloromethane to give the title compound. 1H NMR (500 MHz, CD3CN) δ 7.71 (d, J=7.6 Hz, 1H), 7.61 (dt, J=1.1, 7.6 Hz, 1H), 7.48-7.56 (m, 3H), 7.42 (d, J=7.6 Hz, 1H), 7.12 (t, J=7.9 Hz, 1H), 6.96 (d, J=8.3 Hz, 2H), 6.89 (d, J=8.2 Hz, 2H), 6.78 (q, J=5.4 Hz, 1H), 5.56 (d, J=16.7 Hz, 1H), 5.53 (d, J=16.7 Hz, 1H), 5.24-5.40 (m, 2H), 4.44-4.58 (m, 2H), 4.06-4.18 (m, 2H), 1.7-1.9 (m, 4H), 1.36-1.44 (m, 6H), 1.34 (d, J=6.2 Hz, 3H); LC-MS: m/z 735.3 (M+H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with 3-9% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c53c1ab7ebe44a1eaa998f02d2e99430
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252825B2

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