Ethyl chloroformate → HCID 59139899, compound

Participants

Reaction Steps

According to Scheme 7 Step 5: To a solution of 11(D) (380 mg, 0.92 mmol),) and diisopropylethylamine (189 μL, 1.1 mmol) in THF (10 mL) at 0° C. under nitrogen atmosphere was added ethyl chloroformate (101 μL, 1.06 mmol) dropwise. The reaction mixture was stirred for 1 h then treated dropwise with a solution of sodium borohydride (90 mg, 2.38 mmol) in water (2 mL). The mixture was stirred overnight at room temperature and quenched slowly with a saturated solution of NaHCO3 (100 mL). The aqueous layer was extracted thrice with CH2Cl2 (100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford a yellow solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 20 g SiO2) using CH2Cl2/MeOH 97/3 as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-(hydroxymethyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 11(E) (32 mg, 9%) as a white solid.

Provenance & Evidence