反应详情

1,1,3,3-Tetramethylguanidine (30 μL, 0.24 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 132; 55 mg, 0.11 mmol) in tetrahydrofuran (2 mL) at room temperature. After 5 min, quinoline-3-carboxaldehyde (18 mg, 0.114 mmol) was added and the solution was stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness and the residue was dissolved in a solvent mixture of chloroform/methanol/water/acetic acid (150:30:10:6) and evaporated to dryness. A solution of the residue in a minimum amount of chloroform/methanol/water/acetic acid (150:30:10:6) was applied to a column of three piggy-backed SepPak Plus® silica gel cartridges that had been pre-washed with chloroform. The column was eluted with chloroform, then with a mixture of chloroform/methanol/water/acetic acid (300:30:10:6). Evaporation of the appropriate fractions gave (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (32.7 mg, 55% yield) as a colorless powder.

1. customThe reaction mixture was evaporated to dryness
2. dissolutionthe residue was dissolved in a solvent mixture of chloroform/methanol/water/acetic acid (150:30:10:6)
3. customevaporated to dryness
4. washhad been pre-washed with chloroform
5. washThe column was eluted with chloroform
6. additionwith a mixture of chloroform/methanol/water/acetic acid (300:30:10:6)
7. customEvaporation of the appropriate fractions