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 1173002Notes

Reaction equation

HRID 1173002 reaction equation
[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]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 24958723HCID 24958723, compound

Product 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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ad5f1171dcfc4f3eaaec841421705c6d
Source dataset
uspto-grants-2010_11
Patent number
US07834042B2

Reaction notes

Loading…