Imidazole → HCID 178455368、化合物

HRID 1173823ノート

反応式

HRID 1173823 の反応式
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C1COCC1>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178523817HCID 178523817、化合物

生成物 1

HCID 178455368HCID 178455368、化合物収率 98.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Combine trans-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester (16.0 g, 0.064 mol), imidazole (13.9 g, 0.10 mol), and anhydrous THF (300 mL), add tert-butyldimethylsilyl chloride (14.5 g, 0.10 mol) and stir at room temperature for 18 hours. Wash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL) and dry the organic layer over anhydrous Na2SO4. Remove the solvent and purify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane) to obtain the desired intermediate as clear oil (23.0 g, 98%).

後処理

  1. washWash the reaction mixture with water (250 mL), saturated aqueous NaHCO3 (250 mL)
  2. dry with materialdry the organic layer over anhydrous Na2SO4
  3. customRemove the solvent
  4. custompurify the residue by chromatography over silica gel (eluting with 0 to 30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-3c038cf4aab24e0ab3de0b190b05ae9c
出典データセット
uspto-grants-2010_11
特許番号
US07834194B2

反応ノート

読み込み中…