Water → N-{2-[3-(4-Chloro-phenyl)-5-((R)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carbonyl)-pyridin-2-yloxy]-ethyl}-propionamide

HRID 1929832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929832
[H-].[Na+].[OH:3][CH2:4][CH2:5][NH:6][C:7](=[O:10])[CH2:8][CH3:9].Cl[C:12]1[N:17]=[CH:16][C:15]([C:18]([N:20]2[C@H:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][O:22][C:21]2([CH3:30])[CH3:29])=[O:19])=[CH:14][C:13]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.O>C1COCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:13]2[C:12]([O:3][CH2:4][CH2:5][NH:6][C:7](=[O:10])[CH2:8][CH3:9])=[N:17][CH:16]=[C:15]([C:18]([N:20]3[C@H:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][O:22][C:21]3([CH3:30])[CH3:29])=[O:19])[CH:14]=2)=[CH:32][CH:33]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 87536PropionylaminoethanolHCID 86619570[6-Chloro-5-(4-chloro-phenyl)-pyridin-3-yl]-((R)-4-isobutyl-2,2-dimethyl-oxazolidin-3-yl)-methanone

Produkt 1

HCID 67505397N-{2-[3-(4-Chloro-phenyl)-5-((R)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carbonyl)-pyridin-2-yloxy]-ethyl}-propionamideAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride dispersion in oil (˜55%, 72 mg) was added in portions to a well stirred solution of N-(2-hydroxyethyl)propionamide (71 mg, 0.6 mmol) in THF (13 mL). After stirring the mixture for 15 min at RT [6-Chloro-5-(4-chloro-phenyl)-pyridin-3-yl]-((R)-4-isobutyl-2,2-dimethyl-oxazolidin-3-yl)-methanone (225 mg, 0.55 mmol) was added and stirring continued for 6 h at RT. The mixture was poured into water and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (cyclohexane/ethyl acetate 8:1) to yield 89 mg of the title compound as a white solid, MS (ISP) 488.2 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. dry with materialdried with Na2SO4
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography on silica (cyclohexane/ethyl acetate 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-d25113c6a4074566bba76e811442283b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188093B2

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