反应 #1872101

ord-0ca783e74b7f4afda7fdf29c9133cd08

反应方程式

COC(=O)c1cc(C(=O)OC)cc(N(C)S(C)(=O)=O)c1
dimethyl 5-(N-methylmethylsulfonamido)isophthalate
CCN(C(C)C)C(C)C.ClCCCl.On1nnc2ccccc21
EDC HOBT DIPEA
CNCc1ccccc1
methylbezylamine
→
COC(=O)c1cc(C(=O)NC(C)c2ccccc2)cc(N(C)S(C)(=O)=O)c1
methyl 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoate

反应物

COC(=O)c1cc(C(=O)OC)cc(N(C)S(C)(=O)=O)c1
dimethyl 5-(N-methylmethylsulfonamido)isophthalate
CCN(C(C)C)C(C)C.ClCCCl.On1nnc2ccccc21
EDC HOBT DIPEA
CNCc1ccccc1
methylbezylamine

试剂

无

反应条件

详细条件
See reaction.notes.procedure_details.

实验过程

Dimethyl 5-aminoisophthalate was mesylated by treating with methane sulfonylchloride and pyridine in dichloromethane. Then N-alkylation with methyl iodide under NaH/DMF condition gave dimethyl 5-(N-methylmethylsulfonamnido)isophthalate. Selective hydrolysis of dimethyl 5-(N-methylmethylsulfonamido)isophthalate, followed by EDC/HOBT/DIPEA mediated coupling with cc-methylbezylamine provided methyl 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoate. Ester hydrolysis using aq. 1N NaOH in presence of THF/MeOH provided pure 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoic acid as white solid.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07504420B2uspto-grants-2009_03