反应详情

1,1,3,3-Tetramethylguanidine (20 μL, 0.16 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; 33 mg, 0.066 mmol) in tetrahydrofuran (1 mL) at room temperature. After 5 min, benzaldehyde (7 μL, 0.068 mmol) was added and the solution was stirred at room temperature for 16 h. The solvent was evaporated and the residue was purified by chromatography over silica gel. The column was eluted sequentially with chloroform, chloroform/methanol/water/acetic acid (600:30:10:6), chloroform/methanol/water/acetic acid (300:30:10:6) and chloroform/methanol/water/acetic acid (150:30:10:6). The appropriate fractions were combined and lyophilized to fuirnish (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]-3-phenylpropenoic acid methyl ester (23 mg, 73% yield).

1. customThe solvent was evaporated
2. customthe residue was purified by chromatography over silica gel
3. washThe column was eluted sequentially with chloroform, chloroform/methanol/water/acetic acid (600:30:10:6), chloroform/methanol/water/acetic acid (300:30:10:6) and chloroform/methanol/water/acetic acid (150:30:10:6)