Imidazole → HCID 178455368, 화합물

HRID 1173823노트

반응식

HRID 1173823 반응식
[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

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178523817HCID 178523817, 화합물

생성물 1

HCID 178455368HCID 178455368, 화합물수율 98.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3c038cf4aab24e0ab3de0b190b05ae9c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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