反应 #806284

反应方程式

1,1-Dioxo-2-(4-methoxybenzyl)-3,3-dibutyl-5-phenyl-7-methylthio-8-(t-butoxycarbonylmethoxy)-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine

→

desire product

收率 92.0%

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

收率 92.0%

溶剂

TFA

反应条件

后处理

1. 1
   其他The solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in t-BuOMe (100 ml)
3. 3
   洗涤The organic phase was washed with water (20 ml)
4. 4
   萃取extracted three times with diluted NaOH (2×50 ml 0.5M)
5. 5
   萃取were then extracted twice with t-BuOMe (2×50 ml)
6. 6
   洗涤The ether layer was washed with brine
7. 7
   干燥dried over MgSO4
8. 8
   浓缩concentrated

实验过程

1,1-Dioxo-2-(4-methoxybenzyl)-3,3-dibutyl-5-phenyl-7-methylthio-8-(t-butoxycarbonylmethoxy)-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 25; 6.902 g, 10.11 mmol) was dissolved in a mixture of TFA (50 ml) and Et3Si (8 ml) and the solution was stirred for 90 min at RT. The solvent was removed under reduced pressure and the residue was dissolved in t-BuOMe (100 ml). The organic phase was washed with water (20 ml) and then extracted three times with diluted NaOH (2×50 ml 0.5M). The combined aqueous extracts were acidified with diluted HCl (70 ml, 1M) (pH 1–2) and were then extracted twice with t-BuOMe (2×50 ml). The ether layer was washed with brine, dried over MgSO4 and concentrated. 4.694 g (92%) of the desire product as brown oil were obtained. NMR (400 MHz, CD3OD): 0.70–0.85 (m, 6H), 1.00–1.25 (m, 6H), 1.25–1.50 (m, 4H), 1.55–1.70 (m 2H), 2.10 (s, 3H), 3.90 (brs, 2H), 4.55 (s, 2H), 6.60 (s, 1H), 6.95–7.35 (m, 6H).

来源