反应 #806283

反应方程式

1,1-dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine

NaOH

→

title compound

1,1-Dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine

溶剂

EtOH

反应条件

后处理

1. 1
   其他The solvent was removed under reduced pressure
2. 2
   其他the residue was partitioned between EtOAc and 0.5 M HCl
3. 3
   萃取The aqueous layer was extracted twice more with EtOAc
4. 4
   洗涤the combined organic extracts were washed with brine
5. 5
   浓缩concentrated
6. 6
   其他The crude product was purified by preparative HPLC
7. 7
   其他freeze-dried

实验过程

To a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 1; 0.184 g, 3.24*10−4 mol) in EtOH (7 ml) was added NaOH (0.052 g, 1.30 mmol) and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and 0.5 M HCl. The aqueous layer was extracted twice more with EtOAc and the combined organic extracts were washed with brine and concentrated. The crude product was purified by preparative HPLC using an MeCN/ammonium acetate buffer as eluent and freeze-dried to give the title compound in 0.173 g (99%) as a white solid. NMR (400 MHz, CD3OD) 0.70–0.85 (m, 6H), 0.95–1.70 (m, 12H), 3.90 (brs, 2H), 4.50 (s, 2H), 6.90–7.40 (m, 7H).

来源