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 1173002ノート

反応式

HRID 1173002 の反応式
[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]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 24958723HCID 24958723、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ad5f1171dcfc4f3eaaec841421705c6d
出典データセット
uspto-grants-2010_11
特許番号
US07834042B2

反応ノート

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