반응 #811085

반응 방정식

2-fluoroethylamine hydrochloride

(5R)-3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester

triethylamine

→

title compound

(5R)-N-(2-Fluoroethyl)-3-[4-(4-oxo-3,4-dihydro-1(2H)-pyridinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide

용매

MeOH

반응 조건

후처리

1. 1
   온도The reaction mixture is heated at 50–60° C. for 5 h
2. 2
   기타Solvent is removed
3. 3
   workup.DISSOLUTIONthe residue is dissolved in 20% MeOH/CH2Cl2
4. 4
   기타purified by column chromatography (10% MeOH/CH2Cl2)

실험 절차

To a stirred solution of (5R)-3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid ethyl ester (EXAMPLE 72, Step 5, 226 mg, 0.68 mmol) in MeOH (2 mL) is added triethylamine (0.48 mL, 5.0 equiv.). Then 2-fluoroethylamine hydrochloride (136 mg, 2.0 equiv.) is added to the solution. The reaction mixture is heated at 50–60° C. for 5 h, followed by stirring overnight at room temperature. Solvent is removed and the residue is dissolved in 20% MeOH/CH2Cl2 and purified by column chromatography (10% MeOH/CH2Cl2). The title compound is obtained as a yellow solid (100 mg, 42,%), 1H NMR (300 MHz, DMSO) δ 8.69 (t, 1H), 7.75–7.27 (m, 5H), 5.09 (dd, 1H), 4.98 (d, 1H), 4.55 (t, 1H), 4.39 (t, 1H), 4.29 (t, 1H), 4.02–3.93 (m, 3H), 3.51–3.37 (m, 2H), 2.50–2.45 (m, 2H); MS for C17H18FN3O4 m/z 348.5 (M+H)+.

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