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

HRID 245314Notes

Reaction equation

HRID 245314 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.O1CCCC1>[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 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) and lithium tert-butoxide (0.19 g, 2.4 mmol) were added under nitrogen atmosphere to 10 mL of tetrahydrofuran and the mixture was stirred at room temperature for 2 hours. (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.32 g, 1.1 mmol) was added and then reaction mixture was heated to 60° C. and stirred for 8 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 0.39 g of off-white solid in 82% yield.

Workup

  1. customreaction mixture
  2. temperaturewas heated to 60° C.
  3. stirringstirred for 8 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-cb1f6d8b19e5487e8bc7983c9d838c8d
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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