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

HRID 245369노트

반응식

HRID 245369 반응식
[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

참가 물질

5

반응물 3

HCID 67180Acetone, oximeHCID 23665647Potassium tert-butoxideHCID 178466840HCID 178466840, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-763ea4e068ae4ad89e84208c25db4c6f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658641B2

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