tert-Butyl isocyanate → HCID 68817483, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.2 g (0.44 mmol) of 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester [WO 01/70673, Example 134] in THF (10 mL) at 0° C. was added tert-butylisocyanate (0.130 g, 0.9 mmol). The reaction mixture stirred at 25° C. for 19 h and then the THF was removed in vacuo. The resulting oil was diluted with ethyl acetate (100 mL) and the organics were washed with saturated aqueous sodium chloride (2×30 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column, eluting with an acetonitrile:water gradient, to afford 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-4-carboxylic acid as an amorphous white solid (0.23 g, 96%). MS: 556 (M+H)+.

Provenance & Evidence