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

HRID 245316Notes

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

Conditions

Temperature: 50 °C

Procedure

N-carbobenzoxy-3-fluoro-4-morpholinylaniline (0.33 g, 1 mmol) and lithium tert-butoxide (0.10 g, 1.3 mmol) were added under nitrogen atmosphere to 10 mL of tetrahydrofuran and the mixture was stirred at room temperature for 2 hours (Solution 1). (S)-1-chloro-3-(dibenzylamino)propan-2-ol (0.32 g, 1.1 mmol) and lithium tert-butoxide were added to 10 mL tetrahydrofuran and stirred at room temperature for 2 hours (Solution 2). Solution 2 was added to Solution 1 and the material liquid was heated to 50° C. and reacted 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 0.40 g of off-white solid in 84% yield.

Workup

customreacted for 5 hours
customto separate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-e9deb7946d374231b57b85bde071b9d3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658789B2

Reaction notes

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