반응 #811033

반응 방정식

butyl (5R)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate

fluoroethylamine hydrochloride

→

title compound

(5R)-N-(2-Fluoroethyl)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxamide

용매

CH2Cl2

pyridine

반응 조건

후처리

1. 1
   기타the stirred reaction mixture
2. 2
   기타is placed in an oil bath
3. 3
   온도The mixture is then cooled to ambient temperature
4. 4
   세척washed with 0.2 M hydrochloric acid (25 mL portions
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타the residue is chromatographed on a Flash 40M 90 g silica gel cartridge with MeOH/CH2Cl2 (1/99–2.5/97.5)
8. 8
   농축concentrated
9. 9
   기타the residue triturated
10. 10
    여과filtered from MeOH

실험 절차

A solution of butyl (5R)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 29, Step 2, 985 mg, 2.81 mmol) in pyridine (5.5 mL) in a thick-walled, screw-cap vial is treated with fluoroethylamine hydrochloride (2.20 g, 22.1 mmol), and the stirred reaction mixture is placed in an oil bath maintained at 90° C. for 24 h. The mixture is then cooled to ambient temperature, diluted with CH2Cl2 (50 mL), washed with 0.2 M hydrochloric acid (25 mL portions, until the washings are at pH<2) and saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is chromatographed on a Flash 40M 90 g silica gel cartridge with MeOH/CH2Cl2 (1/99–2.5/97.5). Those fractions with an Rf=0.32 by TLC (MeOH/CHCl3, 5/95) are pooled and concentrated and the residue triturated and filtered from MeOH to give the title compound, mp 201–203° C.; MS (ESI−) for C14H14N3O4FS m/z 338 (M−H)−.

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