Pyridine → Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-(hydroxyimino)acetate

HRID 577906노트

반응식

HRID 577906 반응식
[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24]([C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:23]([F:33])=[C:22]([Cl:34])[C:21]=1[N:35]1[CH2:40][C@H:39]([CH3:41])[O:38][C@H:37]([CH3:42])[CH2:36]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[NH2:50][OH:51]>C(O)(C)C>[Si:1]([O:18][CH2:19][C:20]1[N:25]=[C:24]([C:26](=[N:50][OH:51])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:23]([F:33])=[C:22]([Cl:34])[C:21]=1[N:35]1[CH2:36][C@H:37]([CH3:42])[O:38][C@H:39]([CH3:41])[CH2:40]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 67356587Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate2회

생성물 1

HCID 136385143Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-(hydroxyimino)acetate

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate (Intermediate 121, 13.4 g, 21.85 mmol) was slurried in isopropanol (150 ml), and pyridine (124 ml, 1529.70 mmol) was added to give a yellow solution. Hydroxylamine hydrochloride (1.670 g, 24.04 mmol) was added, and the suspension was stirred at room temperature for approximately 16 hours. The resulting solution was concentrated to an oil. The residue was purified by chromatography on SiO2 using 5-40% EtOAc/hexane. A total of 11.93 g (87%) of the title product as a mixture of oxime isomers was obtained as a yellow oil.

후처리

  1. customto give a yellow solution
  2. concentrationThe resulting solution was concentrated to an oil
  3. customThe residue was purified by chromatography on SiO2 using 5-40% EtOAc/hexane
  4. additionA total of 11.93 g (87%) of the title product as a mixture of oxime isomers
  5. customwas obtained as a yellow oil

출처 및 근거

ORD 기록
ord-4c8d0acf19274337ad66bce9eb413f1c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040528B2

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