Hydrochloric Acid → HCID 60054146, compound

Participants

Reaction Steps

A solution of N-[[(5S)-3-[2-[(acetyloxy)acetyl]-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 3, 230 mg, 0.591 mmol) in MeOH (5.9 mL) is treated with K2CO3 (163 mg, 1.18 mmol), and the resulting mixture is stirred at ambient temperature for 1 hr and is then adjusted to pH 7 with 1M aqueous HCl and concentrated under reduced pressure. The residue is diluted with brine (10 mL) and extracted with CH2Cl2 (3×20 mL), and the combined organic phase is dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of MeOH/CH2Cl2 (2/98-5/95), and those fractions with an Rf=0.25 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated and the residue triturated with Et2O to give 146 mg (71%) of the title compound as an amorphous, white solid. MS (ESI+) for C17H21N3O5 m/z 348 (M+H)+; [α]25D=−18° (c 0.96, DMSO); Anal. Calcd for C17H21N3O5: C, 58.78; H, 6.09; N, 12.10. Found: C, 58.59; H, 6.49; N, 11.77.

Provenance & Evidence