Hydrochloric Acid → 3-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

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Reaction Steps

HCl gas was bubbled through a stirred suspension of 2-[6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl]acetic acid t-butyl ester (16-3; 12.3 g, 33 mmol) in ethyl acetate (250 ml) at −15° C. for 20 min. The resulting solution was allowed to warm to room temperature and was then stirred there for 3 h. After purging with argon, the bulk of the solvent was rotavapped off and ether added to the residue. The solid which precipitated was filtered off and washed with ether. The title compound 16-4 was thus obtained as a white fluffy powder: 1H NMR (CD3OD) δ 2.32 (s, 3H), 4.86 (s, 2H), 5.18 (s, 2H), 6.24 (d, J=7.9 Hz, 1H), 7.31-7.41 (m, 6H), 7.94 (br s, 1H).

Provenance & Evidence