Pyridine → HCID 11416753, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of carboxytetrazole (5, 0.05 g, 0.2 mmol) in CH2Cl2 (5 mL) at 0° C. under N2 was added DMF (4-drops) followed by (COCl)2 (IM CH2Cl2, 0.15 mL, 0.3 mmol) and the reaction was stirred for 1 h. The reaction solvent was removed and the resulting residue of acid chloride was dried under high vacuum. The acid chloride was then suspended in CH2Cl2 (5 mL), cooled to 0° C., to it was added pyridine (0.033 mL, 0.4 mmol) followed by H2N-OTHP (0.035 g, 0.3 mmol), and stirred at room temperature for 24 h. The CH2Cl2 solution was washed with water, dried and solvent was evaporated. The resulting residue was filtered through a pad of silica gel to obtain the requisite oxamic acid ester 6. 1H NMR (CDCl3): δ 11.58 (s, 1H), 8.92 (s, 1H), 8.74 (d, 1H, J=1.8 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.77 (dd, 1H, J=1.8 Hz and 8.7 Hz), 5.26 (m, 1H), 4.15 (m, 1H), 3.76 (m, 1H), 2.10-1.50 (m, 6H); LCMS (ret. time): 21.46 min.; MS (m/z): 347 (MH+).

Provenance & Evidence