Ammonium Chloride → (S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

HRID 245313

Reaktionsgleichung

Reaktionsgleichung von HRID 245313
[C:1]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([F:24])[CH:13]=1)([O:3][CH2:4][C:5]1C=CC=CC=1)=[O:2].CC(C)([O-])C.[Li+].ClC[C@@H](O)[CH2:34][N:35]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[CH2:43]([N:35]([CH2:34][C@@H:4]1[O:3][C:1](=[O:2])[N:11]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[C:14]([F:24])[CH:13]=2)[CH2:5]1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 5306150Carbamic acid, N-(3-fluoro-4-(4-morpholinyl)phenyl)-, phenylmethyl esterHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 49765557(S)-1-chloro-3-(dibenzylamino)propan-2-ol

Produkt 1

HCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-oneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) was added under nitrogen atmosphere to 5 mL of DMF (N,N-dimethyl formamide), and mixture was cooled to −10˜0° C. A solution of lithium tert-butoxide (2.5 mL, 2.5 mmol) in tetrahydrofuran was added dropwise. The mixture was warmed to room temperature (25° C.) naturally and stirred for 2 hours. (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.32 g, 1.1 mmol) was then added and the mixture was stirred at room temperature for 20 hours. Saturated ammonium chloride solution and ethyl acetate were added to separate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 0.42 g of white solid in 88% yield.

Aufarbeitung

  1. temperaturewas cooled to −10˜0° C
  2. stirringthe mixture was stirred at room temperature for 20 hours
  3. customto separate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-66f0e0c18c8b4dc1b924d7ee7db236c9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658789B2

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