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 1361906Notes

Reaction equation

HRID 1361906 reaction equation
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]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178441694HCID 178441694, compound

Product 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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d165420ddb1d4af49ab6b4302d7f563a
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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