Water → [4-(2-Methoxy-ethoxymethyl)-thiazol-2-yl]-carbamic acid phenyl ester

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Reaction Steps

tert-butyl 4-((2-methoxyethoxy)methyl)thiazol-2-ylcarbamate (Intermediate III, 3.4 g, 0.018 mol) was dissolved in pyridine (50 mL) and a catalytic amount of DMAP was added (0.2 g, ˜10 mol %). To this mixture a solution of phenyl chloroformate (2.27 mL, 1 eq.) in THF (50 mL) was added drop wise and the resulting reaction mixture was stirred for 3 hours at ambient temperature. Then, H2O was added and the diluted mixture was extracted with EtOAc. Dried the organic layer over Na2SO4, filtered and concentrated in vacuo. Purification over SiO2 eluting with 1:1 EtOAc/heptane gave 2.4 gram of the product as a yellow fluffy solid. 1H-NMR (300 MHz, DMSO-d6) δ 11.70 (s, br, 1H), 7.42 (d, 1H), 7.37 (m, 1H), 7.08 (m, 3H), 4.59 (s, 2H), 4.38 (d, 2H), 3.30 (s, 2H), 3.23 (t, 2H), 1.75 (q, 2H), 0.97 (t, 3H).

Provenance & Evidence