反应 #3361

反应方程式

2-[2-(1-carboxy-2-methylbutylcarbamoyl) phenyldisulfanylbenzoylamino]-3-methylpentanoic acid

bromine

→

title compound

3-Methyl-2-(3-oxo-3h-benzo[d]isothiazol-2-yl)pentanoic acid

溶剂

dichloromethane

反应条件

后处理

1. 1
   浓缩concentrated to dryness in vacuo
2. 2
   其他The residue was triturated with dichloromethane
3. 3
   其他The dichloromethane was removed by evaporation in vacuo
4. 4
   其他to remove excess bromine
5. 5
   其他The residue was partitioned between dichloromethane/5% aqueous sodium bicarbonate (200 mL each)
6. 6
   其他The aqueous layer was separated
7. 7
   洗涤washed with fresh dichloromethane
8. 8
   萃取The acidic aqueous solution was extracted with dichloromethane (2×75 mL)
9. 9
   洗涤washed with water
10. 10
    干燥dried (MgSO4)
11. 11
    过滤filtered
12. 12
    浓缩concentrated to dryness in vacuo

实验过程

To a stirred suspension of 5.3 g (10.0 mmol) of [S-(R*,R*)]-2-[2-[2-(1-carboxy-2-methylbutylcarbamoyl) phenyldisulfanylbenzoylamino]-3-methylpentanoic acid (from Preparation 19) in 200 mL of dichloromethane was added dropwise 2.4 g (15.0 mmol) of liquid bromine. The reaction mixture was stirred at room temperature for 2 hours and concentrated to dryness in vacuo. The residue was triturated with dichloromethane. The dichloromethane was removed by evaporation in vacuo to remove excess bromine. The residue was partitioned between dichloromethane/5% aqueous sodium bicarbonate (200 mL each). The aqueous layer was separated, washed with fresh dichloromethane, and acidified to pH 1.5 with 6.0M hydrochloric acid. The acidic aqueous solution was extracted with dichloromethane (2×75 mL). The organic layers were combined, washed with water, dried (MgSO4), filtered and concentrated to dryness in vacuo to give 4.8 g of the title compound, mp 50°-52° C.

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