4-Methylmorpholine → (R)-3-{4-[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one hydrochloride

HRID 1804207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804207
[CH3:1][C@@H:2]1[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[ClH:17].[CH:18]1([C:21]2[C:22]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=2)[CH2:20][CH2:19]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[ClH:17].[CH:18]1([C:21]2[C:22]([N:28]3[CH2:33][CH2:32][N:31]([C:12]([C:11]4[CH:10]=[CH:9][C:8]([N:3]5[C@H:2]([CH3:1])[CH2:6][O:5][C:4]5=[O:7])=[CH:16][CH:15]=4)=[O:14])[CH2:30][CH2:29]3)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=2)[CH2:19][CH2:20]1

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 673807751-(3-Cyclopropyl-5-methylpyridin-2-yl)piperazine hydrochloride

Produkt 1

HCID 67381384(R)-3-{4-[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one hydrochlorideAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (442 mg) described in Preparation Example 37, 1-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine hydrochloride (435 mg) described in Preparation Example 48 and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (829 mg) were dissolved in chloroform (3 mL) and methanol (3 mL), N-methylmorpholine (220 μL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate). The obtained compound was dissolved in ethyl acetate (20 mL), 4N hydrogen chloride/ethyl acetate (0.5 mL) was added, and the mixture was filtered to give the title compound (652 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (hexane:ethyl acetate)
  5. dissolutionThe obtained compound was dissolved in ethyl acetate (20 mL)
  6. addition4N hydrogen chloride/ethyl acetate (0.5 mL) was added
  7. filtrationthe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-15db2adbff2b46d48e95c23a89a32d9f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

Notizen zur Reaktion

Wird geladen…