Dicyclohexylcarbodiimide → (4S)-3-({[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetyl)-4-phenyl-1,3-oxazolidin-2-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

{[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid (9.9 g, 33.0 mmol) was dissolved in dry CH2Cl2 (250 ml) and cooled to 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 7.63 g, 37.0 mmol) and 4-(dimethylamino)pyridine (DMAP, 8.57 g, 70.0 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (5.38 g, 33.0 mmol) was added and the mixture was stirred at room temperature for 70 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc-7:3). This afforded 10.2 g (70%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): 0.6 (s, 3H), 1.3 (s, 3H), 2.8 (s, 2H), 3.4 (s, 4H), 3.8 (s, 2H), 4.1-4.15 (dd, 1H), 4.6-4.8 (t, 1H), 5.35-5.45 (dd, 1H), 7.25-7.45 (m, 9H).

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