Isoguvacine → 1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid

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Reaction Steps

A solution of 2-chloro-pyridine-3-sulfonic acid dimethylamide (1.18 mmol) and isoguvacine, sodium salt (2.19 mmol) in THF (0.5 mL) and water (2 mL) was stirred at 90° C. for 22 hours, acidified (pH˜1) with TFA, and extracted with CH2Cl2. The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography (5% MeOH/CH2Cl2) and trituration (Et2O) to provide as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.47 (dd, J=1.7, 4.8 Hz, 1H), 8.22 (dd, J=1.7, 7.8 Hz, 1H), 7.22 (dd, J=4.8, 7.8 Hz, 1H), 7.03 (sept, J=1.7 Hz, 1H), 3.99 (q, J=3.0 Hz, 2H), 3.40 (t, J=5.6 Hz, 2H), 2.73 (s, 6H), 2.56 (m, 2 H).

Provenance & Evidence