2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methoxy-n-(4-methylbenzyl)-acetamide → 2-Hydroxy-3-[methoxy-(4-methylbenzyl)-carbamoyl]-acrylic acid methyl ester

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Reaction Steps

2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-N-(4-methylbenzyl)-acetamide, prepared using the methods described in the previous examples, was treated with methanol as described in the preparation of Compound 44-D to give the title ester as white crystals (69% yield); mp 83–84° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.59 (3H, s, CH3), 3.94 (3H, s, OCH3), 4.15 (3H, s, OCH3), 5.05 (2H, s, NCH2), 6.72 (1H, s, CH), 7.41 (2H, d, J=8.1 Hz, aromatics), 7.47 (2H, d, J=8.1 Hz, aromatics), 13.75 (1H, broad s, OH). Anal. calcd for C14H17NO5: C, 60.20; H, 6.13; N, 5.01. Found: C, 60.24; H, 6.09; N, 4.85.

Provenance & Evidence