Dimethyl Sulfoxide → HCID 68584830、化合物

HRID 17326ノート

反応式

HRID 17326 の反応式
C(N(CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CS(C)=O.[C:29]([C:33]1[O:34][C:35]2[C:36](=[C:38]([C:50]#[N:51])[C:39]([CH3:49])=[C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:41]=2F)[N:37]=1)([CH3:32])([CH3:31])[CH3:30]>C(OCC)(=O)C>[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:41]2[C:40]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[C:39]([CH3:49])[C:38]([C:50]#[N:51])=[C:36]3[C:35]=2[O:34][C:33]([C:29]([CH3:32])([CH3:30])[CH3:31])=[N:37]3)[CH2:20]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1514175Benzyl (3S)-piperidin-3-ylcarbamateHCID 685846072-Tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 68584830HCID 68584830、化合物収率 75.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

Triethylamine (83 μl, 598 μmol) and (3S)-3-benzyloxycarbonylaminopiperidine (70 mg, 298 μmol) were added to a dimethyl sulfoxide (3.8 ml) solution of 2-tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-72) (77 mg, 249 μmol), followed by stirring at 90° C. for 11 hours. After cooling, the reaction liquid was diluted with ethyl acetate, this was washed with saturated brine and 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→4:1, v/v) to obtain the entitled compound (98 mg, 75%) as a colorless oil.

後処理

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. washthis was washed with saturated brine and 1 N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane

出典と根拠

ORDレコード
ord-8d15c92b38f44c1eb3f0c734630f170e
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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