Formic Acid → HCID 60054145, compound

Participants

Reaction Steps

A solution of N-[[(5S)-3-[1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 1, Step 6, 200 mg, 0.691 mmol) in THF is treated with EDC.HCl (172 mg, 0.899 mmol) and formic acid (34 μL, 0.899 mmol) to give a white slurry which is then diluted with H2O (approx. 2 mL) to give a homogeneous mixture. The mixture is stirred at ambient temperature for 1.25 hrs and is then diluted with H2O (10 mL) and extracted with CH2Cl2 (4×20 mL). The combined organic phase is washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure, and the crude product is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of MeOH/CH2Cl2 (1/99-5/95). Those fractions with an Rf=0.41 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated and the resulting glassy solid is triturated with Et2O and filtered to give 161 mg (74%) of the title compound as a white solid, mp 139-141° C. (dec.). [α]25D=−22° (c 0.92, DMSO).

Provenance & Evidence