1H-Benzotriazole-1-carboxaldehyde → HCID 86594252, compound

Participants

Reaction Steps

A solution of 1,1-dimethylethyl [[(5S)-2-oxo-3-[1,2,3,4-tetrahydro-6-isoquinolinyl]-5-oxazolidinyl]methyl]carbamate (Step 2, 292 mg, 0.841 mmol) in dry THF (16.8 mL) is treated with 1H-benzotriazol-1-carboxaldehyde (148 mg, 1.01 mmol), and the resulting suspension is stirred at ambient temperature for 1.25 hrs and is then concentrated to remove THF. The residue is rediluted with CH2Cl2 (25 mL), washed with 1N aqueous NaOH (2×10 mL) and brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure to give the crude product which is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with MeOH/CH2Cl2 (2.5/97.5). Those fractions with an Rf=0.60 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated to give 310 mg (98%) of the title compound as an amorphous, glassy solid. MS (ESI+) for C19H25N3O5 m/z 376 (M+H)+.

Provenance & Evidence