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

HRID 245450
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 245450
[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
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Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 67356587Ethyl 2-(6-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-((2R,6S)-2,6-dimethylmorpholino)-3-fluoropyridin-2-yl)-2-oxoacetate2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-024f7ee0464a43e78609a4d409649a12
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658641B2

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