Dimethylformamide → 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

HRID 889520ノート

反応式

HRID 889520 の反応式
CN(C)C=O.[C:6](=[O:26])([O:22][CH:23](Cl)[CH3:24])[O:7][CH2:8][CH2:9][CH2:10][C@@H:11]([O:18][N+:19]([O-:21])=[O:20])[C@H:12]([O:14][N+:15]([O-:17])=[O:16])[CH3:13].[CH2:27]([O:29][C:30]1[N:34]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[N:51]=[N:50][N:49]=3)=[CH:38][CH:37]=2)[C:33]2[C:72]([C:76]([OH:78])=[O:77])=[CH:73][CH:74]=[CH:75][C:32]=2[N:31]=1)[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH2:27]([O:29][C:30]1[N:34]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)[N:51]=[N:50][N:49]=3)=[CH:40][CH:41]=2)[C:33]2[C:72]([C:76]([O:78][CH:23]([O:22][C:6]([O:7][CH2:8][CH2:9][CH2:10][C@@H:11]([O:18][N+:19]([O-:21])=[O:20])[C@H:12]([O:14][N+:15]([O-:17])=[O:16])[CH3:13])=[O:26])[CH3:24])=[O:77])=[CH:73][CH:74]=[CH:75][C:32]=2[N:31]=1)[CH3:28]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 10796Cesium carbonateHCID 103125632-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acidHCID 86647015(4R,5R)-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

生成物 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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A N,N-dimethylformamide (20 mL) solution of (4R,5R)-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate (2.94 g, 8.89 mmol) was added to a stirred N,N-dimethylformamide (20 mL) suspension of 2-ethoxy-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid (7.46 g, 10.9 mmol) and cesium carbonate (3.95 g, 12.1 mmol). The solution was stirred at 70° C. for 2 hours. Water (100 mL) was added, and the solution was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with 20-60% ethyl acetate/hexanes to give the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.84 (dd, J=1.6, 7.3 Hz, 1H), 7.76 (dd, J=1.0, 7.9 Hz, 1H), 7.58 (dd, J=1.0, 7.9 Hz, 1H), 7.45 (dt, J=1.7, 7.4 Hz, 1H), 7.42 (dt, J=1.7, 7.4 Hz, 1H), 7.32 (t, J=7.4 Hz, 3H), 7.29 (dd, J=1.5, 7.4 Hz, 1H), 7.24 (t, J=7.8 Hz, 6H), 7.17 (t, J=7.9 Hz, 1H), 6.98 (d, J=8.2 Hz, 2H), 6.92 (d, J=8.2 Hz, 6H), 6.85 (q, J=5.4 Hz, 1H), 6.78 (d, J=8.2 Hz, 2H), 5.56 (s, 2H), 5.12-5.22 (m, 2H), 4.58-4.68 (m, 2H), 4.06-4.20 (m, 2H), 1.64-1.94 (m, 4H), 1.41-1.46 (m, 6H), 1.33 (d, J=6.4 Hz, 3H); LC-MS: m/z 999.5 (M+Na).

後処理

  1. extractionthe solution was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with 20-60% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-2dac838d4af54667aca4735a8211cad2
出典データセット
uspto-grants-2012_08
特許番号
US08252825B2

反応ノート

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