1-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate → HCID 178441698, compound

HRID 889518Notes

Reaction equation

HRID 889518 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]3[N:51](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:50]=[N:49][N:48]=3)=[CH:37][CH:36]=2)[C:7]([C:11]([O:13][CH:14]([O:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][C@@H:23]([O:30][N+:31]([O-:33])=[O:32])[C@H:24]([O:26][N+:27]([O-:29])=[O:28])[CH3:25])=[O:18])[CH3:15])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]>CO>[CH2:1]([C:5]1[N:6]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]3[NH:51][N:50]=[N:49][N:48]=3)=[CH:37][CH:36]=2)[C:7]([C:11]([O:13][CH:14]([O:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][C@@H:23]([O:30][N+:31]([O-:33])=[O:32])[C@H:24]([O:26][N+:27]([O-:29])=[O:28])[CH3:25])=[O:18])[CH3:15])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 866470161-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

Product 1

HCID 178441698HCID 178441698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A methanol (30 mL) suspension of 1-[({[(4R,5R)-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate (1.63 g, 1.68 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 (dd, J=0.9, 7.8 Hz, 1H), 7.64 (dt, J=1.2, 7.6 Hz, 1H), 7.54 (dt, J=1.1, 7.6 Hz, 1H), 7.51 (d, J=7.5 Hz, 1H), 7.10 (d, J=8.2 Hz, 2H), 6.98 (d, J=8.0 Hz, 2H), 6.81 (q, J=5.5 Hz, 1H), 5.53 (d, J=16.7 Hz, 1H), 5.48 (d, J=17.1 Hz, 1H), 5.25-5.35 (m, 2H), 4.11 (t, J=5.8 Hz, 2H) 2.60 (t, J=7.7 Hz, 2H), 1.70-1.84 (m, 4H), 1.58 (quintet, J=7.6 Hz, 2H), 1.49 (d, J=5.5 Hz, 3H), 1.35 (d, J=6.3 Hz, 3H), 1.31 (sextet, J=7.5 Hz, 2H), 0.85 (t, J=7.4 Hz, 3H); LC-MS: m/z 731.3 (M+H).

Workup

  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

Sources & evidence

ORD record
ord-95bfa4ed5ecc4aa4b47d48a569c8fde2
Source dataset
uspto-grants-2012_08
Patent number
US08252825B2

Reaction notes

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