Triethylamine → Ethyl [({[4-(acetyloxy)-3-methoxybenzyl]oxy}carbonyl)amino]acetate

Participants

Reaction Steps

Thiazolide VII (266.8 mg, 0.781 mmol) was dissolved in anhydrous THF (3 mL), and the resulting solution was added to a previously prepared solution of ethyl glycinate (130 mg, 1.19×0.781 mmol) and diisopropylethylamine (120 mg, 162 μL, 1.19×0.781 mmol) in chloroform (3 mL). To the resulting solution was added triethylamine (72.6 mg, 100 μL, 0.72 mmol) at which point a slight cloudiness developed. The mixture was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 and extracted with 1N HCl and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The product was purified by column chromatography on silica gel using a gradient of CH2Cl2/ethyl acetate (94:6-9:1, v/v) to yield 152.9 mg (60%) of a white solid 19: mp=62-64° C. (uncorrected); Rf=0.27 (CH2Cl2/EtOAc, 96:4, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8 Hz, 1H), 6.96 (bs, 1H), 6.92 (bd, 3J=8 Hz, 1H), 5.22 (bs, 1H), 5.08 (bs, 2H), 4.20 (q, 3J=7.15 Hz, 2H), 3.96 (d, 3J=5.55 Hz, 2H), 3.82 (s, 3H), 2.29 (s, 3H) and 1.27 (t, 3J=7.15 Hz, 3H). Exact mass (ESI) calculated for C15H20NO7 [M+H]=326.1234. found 326.1245.

Provenance & Evidence