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

HRID 245332Notes

Reaction equation

HRID 245332 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(#N)C>[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 60%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) was added to 8 mL acetonitrile. The solution was cooled to −30° C. under the protection of nitrogen flow and then 50 mmol lithium tert-butoxide was added. The mixture reacted at −30° C.˜−20° C. for 2 hours. (S)-1-chloro-3-(dibenzylamino)propan-2-ol (1.45 g, 5 mmol) was added and then the solution was heated slowly to 60° C. and the reaction was maintained for 2 hours. After the solution was cooled down, 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 evaporated to dryness to provide 285 mg of white solid in 60% yield. HPLC: 99.2%.

Workup

  1. customThe mixture reacted at −30° C.˜−20° C. for 2 hours
  2. temperaturethe solution was heated slowly to 60° C.
  3. temperaturethe reaction was maintained for 2 hours
  4. temperatureAfter the solution was cooled down
  5. customto separate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-8f7c4d7046874b59bd4262772248d62b
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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