Pyridine → 1-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}-2,2,2-trifluoro-N-hydroxyethanimine

HRID 577903노트

반응식

HRID 577903 반응식
N1C=CC=CC=1.[Si:7]([O:24][CH2:25][C:26]1[C:27]([N:40]2[CH2:45][C@H:44]([CH3:46])[O:43][C@H:42]([CH3:47])[CH2:41]2)=[C:28]([F:39])[C:29]([F:38])=[C:30]([C:32](=O)[C:33]([F:36])([F:35])[F:34])[CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[NH2:49][OH:50]>C(O)C>[Si:7]([O:24][CH2:25][C:26]1[C:27]([N:40]2[CH2:41][C@H:42]([CH3:47])[O:43][C@H:44]([CH3:46])[CH2:45]2)=[C:28]([F:39])[C:29]([F:38])=[C:30]([C:32](=[N:49][OH:50])[C:33]([F:36])([F:35])[F:34])[CH:31]=1)([C:20]([CH3:21])([CH3:23])[CH3:22])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866580921-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2,2,2-trifluoroethanone2회

생성물 1

HCID 866580911-{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}-2,2,2-trifluoro-N-hydroxyethanimine수율 100.1%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

Pyridine (2597 μl, 32.11 mmol) was added to a mixture of 1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2,2,2-trifluoroethanone (Intermediate 130, 1900 mg, 3.21 mmol) and hydroxylamine hydrochloride (223 mg, 3.21 mmol) in 50 ml of ethanol and the solution was heated at 80° C. for 40 hours. The reaction mixture was concentrated, diluted with water, and extracted with ethyl acetate. The organic phases were combined, dried (Na2SO4), and concentrated to give the crude title compound (1.95 g, 98%), which was used in the next step without further purification.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-049607b4b2e445a895b93889ead84396
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040528B2

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