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

HRID 245315

Reaction equation

HRID 245315 reaction equation
[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+]>C(OCC)(=O)C.C(Cl)Cl>[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

Participants

7

Reactant 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

Product 1

HCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-oneYield 69.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-carbobenzoxy-3-fluoro-4-morpholinyl aniline (0.33 g, 1 mmol) and lithium tert-butoxide (0.19 g, 2.4 mmol) were added under nitrogen atmosphere to 10 mL of methylene dichloride and the mixture was stirred at room temperature for 0.5 hours. (S)-1-chloro-3-(dibenzylamino) propan-2-ol (0.32 g, 1.1 mmol) was added and the reaction mixture was heated to reflux and stirred for 5 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 0.33 g of off-white solid in 69% yield.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. stirringstirred for 5 hours
  4. customto separate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c600a7b9783149b2a5dcd50621392032
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Linked notes

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