Tetrabutylammonium Fluoride → (Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester

Participants

Reaction Steps

To a solution of (Z)-2-[[4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (47 mg, 0.0773 mmol) in THF (1 mL) was added a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.085 mmol, 85 μL) and the reaction was stirred for 3 days at ambient temperature. The reaction was diluted with ethyl acetate and was then washed with in turn with water and brine. The organic layer was dried (MgSO4), filtered and evaporated in vacuo to yield 39 mg of (Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester as a yellow solid (quantitative yield).

Provenance & Evidence