Ethyl Acetate → Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 265049ノート

反応式

HRID 265049 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:14]1[N:15]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[N:46]([C:47]([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)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:45]=[N:44][N:43]=3)=[CH:32][CH:31]=2)[C:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:17]([C:19](OCC)=[O:20])[N:18]=1)[CH2:12][CH3:13].C(OCC)(=O)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[OH:20][CH2:19][C:17]1[N:18]=[C:14]([CH2:11][CH2:12][CH3:13])[N:15]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[N:46]([C:47]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[N:45]=[N:44][N:43]=3)=[CH:34][CH:35]=2)[C:16]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19036089Diethyl 2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-4,5-dicarboxylateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 19036205Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate収率 100.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

10 ml of a 1.5M solution of diisobutylaluminum hydride in toluene were added dropwise at -20° C. under an atmosphere of nitrogen to a solution of 4.27 g of diethyl 2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-4,5-dicarboxylate [prepared as described in step (a) above] in 50 ml of tetrahydrofuran. The resulting mixture was allowed to stand at 0° C. for 16 hours and then mixed with ethyl acetate and with a saturated aqueous solution of ammonium chloride; it was then stirred at room temperature for 1 hour. The resulting precipitate was filtered off, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure. The crystalline residue was washed with diisopropyl ether, to give 4.03 g of the title compound, melting at 135°-138° C.

後処理

  1. filtrationThe resulting precipitate was filtered off
  2. customthe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation under reduced pressure
  5. washThe crystalline residue was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-7f09f487e8494b70bc1ccc65188eab85
出典データセット
uspto-grants-1997_07
特許番号
US05646171

反応ノート

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