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

HRID 577906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577906
[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

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-4c8d0acf19274337ad66bce9eb413f1c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040528B2

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