Ethanol → (5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

HRID 245335Notes

Reaction equation

C([N:8]([CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)CC1C=CC=CC=1)C1C=CC=CC=1.C(O)C.N#N>[Pd].O.C(N(CC)CC)C.C(O)=O>[NH2:8][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 4 (0.95 g, 2 mmol) and 10% Pd—C (1 mmol) were added to the mixture of 20 mL of ethanol and 2 mL of water and the air was replaced with N2. The triethylamine-Formic acid azeotrope (704 mg, 4 mmol) was added and the mixture was stirred at 80° C. for 12 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 0.49 g of white solid in 84% yield. HPLC: 99.3%.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-9639805796db427d8847975baf2f6e04
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658789B2

Reaction notes

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