Acetone, oxime → 1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-3-fluoro-2-(propan-2-ylideneaminooxy)phenyl)ethanone

HRID 245369ノート

反応式

HRID 245369 の反応式
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].C[C:7]([O-])([CH3:9])[CH3:8].[K+].[C:12]([SiH2:16][O:17][C:18](C1C=CC=CC=1)(C1C=CC=CC=1)[C:19]1[C:20]([N:30]2[CH2:35][C@H:34]([CH3:36])[O:33][C@H:32]([CH3:37])[CH2:31]2)=[C:21]([F:29])[C:22](F)=[C:23]([C:25](=[O:27])[CH3:26])[CH:24]=1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[Si:16]([O:17][CH2:18][C:19]1[C:20]([N:30]2[CH2:31][C@H:32]([CH3:37])[O:33][C@H:34]([CH3:36])[CH2:35]2)=[C:21]([F:29])[C:22]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])=[C:23]([C:25](=[O:27])[CH3:26])[CH:24]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([C:8]1[CH:7]=[CH:9][CH:14]=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 67180Acetone, oximeHCID 23665647Potassium tert-butoxideHCID 178466840HCID 178466840、化合物2 回

生成物 1

HCID 866580551-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-3-fluoro-2-(propan-2-ylideneaminooxy)phenyl)ethanone収率 203%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of propan-2-one oxime (913 mg, 12.50 mmol) in THF (15 ml) was added KOtBu (935 mg, 8.33 mmol) at room temperature. After stirring for 45 minutes, 1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}ethanone (Intermediate 9, 2240 mg, 4.17 mmol) dissolved in 10 ml of THF was added. After stirring for 3 hours reaction quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated to give the crude title compound (2.5 g). LCMS and NMR indicates >90% purity. Used in the next step without any further purification.

後処理

  1. additionwas added
  2. stirringAfter stirring for 3 hours
  3. customreaction
  4. customquenched with saturated aqueous ammonium chloride solution
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-763ea4e068ae4ad89e84208c25db4c6f
出典データセット
uspto-grants-2014_02
特許番号
US08658641B2

反応ノート

読み込み中…