Ethyl Acetate → (S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

HRID 1850216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850216
C(O[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OCC)OCC)C.[CH:17]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]([CH3:38])[C:34]([NH:36][NH2:37])=[O:35])[N:27]=1)([CH3:19])[CH3:18].C(OCC)(=O)C>CCCCCCC>[CH:17]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@H:33]([C:34]2[O:35][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:37][N:36]=2)[CH3:38])[N:27]=1)([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 74268Benzene, (triethoxymethyl)-HCID 86730168(S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazide

Produkt 1

HCID 86730271(S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-oneAusbeute 17,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

A solution of (triethoxymethyl)benzene (360 mg, 1.6 mmol, 5.0 equiv. in 5 mL of benzene and 0.5 mL of glacial AcOH) was added to (S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazide (99 mg, 0.30 mmol, 1.0 equiv.), the reaction mixture was stirred at reflux for 1.5 hours, the solvent was removed to yield the crude product. Silica gel column chromatography (ethyl acetate in heptane 10 to 90%) to yield (S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (21.2 mg, white solid) in 15.9% yield. HRMS(B) m/z 395.1820, (M+H)+, RT=2.42 min

Aufarbeitung

  1. temperatureat reflux for 1.5 hours
  2. customthe solvent was removed
  3. customto yield the crude product

Quellen und Nachweise

ORD-Eintrag
ord-570d6f198e06499fa4b3f4a5410e5e3c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957068B2

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