Methyl chloroformate → HCID 60054152, compound

Participants

Reaction Steps

A mixture of N-[[(5S)-3-[1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Step 6, 450 mg, 1.55 mmol) and NaHCO3 (260 mg, 3.10 mmol) in THF (15.5 mL) under N2 is treated with methyl chloroformate (0.144 mL, 1.87 mmol) with vigorous stirring. A thick, white slurry results which is redissolved by the addition of H2O (approx. 2 mL). The mixture is stirred at ambient temperature for 1 hr and is then diluted with H2O (10 mL) and EtOAc (20 mL) and the layers are separated. The aqueous phase is reextracted with CH2Cl2 (20 mL), and the combined organic phase is washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product is chromatographed on silica gel (45 g, 230-400 mesh), eluting with MeOH/CHCl3 (2/98), and those fractions with an Rf=0.51 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated to give 475 mg (88%) of the title compound as a glassy solid. 1H NMR (400 MHz, CDCl3) δ 7.32 (m, 2H), 7.11 (m, 1H), 6.19 (m, 1H), 4.76 (m, 1H), 4.59 (s, 2H), 4.05 (t, 1H), 3.78 (dd, 1H), 3.75 (s, 3H), 3.75-3.50 (m, 4H), 2.85 (m, 2M), 2.02 (s, 3H); MS (ESI+) for C17H21N3O5 m/z 348 (M+H)+; [α]25D=−20° (c 1.04, DMSO).

Provenance & Evidence