海萝胶 → N-[2-(tert-Butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17388

反应方程式

HRID 17388 反应方程式
C[Al](C)C.[O:5]([CH2:23][CH2:24][NH:25][CH3:26])[Si:6]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:27]([C:29]1[C:34]2[N:35]=[C:36]([C:38](OCC)=[O:39])[O:37][C:33]=2[C:32]([F:43])=[C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:30]=1[CH3:50])#[N:28].Cl>ClCCl>[O:5]([CH2:23][CH2:24][N:25]([CH3:26])[C:38]([C:36]1[O:37][C:33]2[C:32]([F:43])=[C:31]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:30]([CH3:50])=[C:29]([C:27]#[N:28])[C:34]=2[N:35]=1)=[O:39])[Si:6]([C:19]([CH3:20])([CH3:21])[CH3:22])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参与物

6

反应物 4

HCID 313海萝胶HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineHCID 16682925三甲基铝HCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

产物 1

HCID 68584854N-[2-(tert-Butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide收率 67%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

实验过程

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 1.05 ml, 1.54 mmol) was dropwise added at room temperature to a dichloromethane (3 ml) solution of [2-(tert-butyldiphenylsiloxy)ethyl]methylamine (I-123) (483 mg, 1.54 mmol), and stirred for 40 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (250 mg, 771 μmol) was dropwise added and stirred for 16 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with n-hexane/ethyl acetate (3:1, v/v) gave the entitled compound (304 mg, 67%) as an amorphous substance.

后处理

  1. stirringstirred for 16 hours
  2. additionwas added to the reaction liquid
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature
  5. customthe reaction liquid
  6. extractionwas extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

来源与证据

ORD记录
ord-3845eb9830c14e3db50799986058482e
来源数据集
uspto-grants-2010_06
专利号
US07737166B2

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