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

HRID 17388

反応式

HRID 17388 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3845eb9830c14e3db50799986058482e
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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