Ethyl bromoacetate → HCID 86616402, Verbindung

Reaktionsgleichung

[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C@@H:3]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14][C@H:2]12.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[O:7]=[C:5]1[CH2:6][O:1][C@H:2]2[CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C@H:3]2[N:4]1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Komponenten

Versuchsvorschrift

To a solution of (4aR,9aS)-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one from Step B (600 mg, 3.17 mmol) in DMF (15 mL) at 0° C. was added NaH (228 mg of a 60% dispersion in oil, 5.71 mmol) and the resulting mixture was stirred for 10 min. Ethyl bromoacetate (0.288 mL, 3.5 mmol) was added and the reaction mixture was stirred for 18 h. The reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL) and then extracted with EtOAc (2×40 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc 80:20 to 0:100, to give the title compound. MS: m/z=276 (M+1)