반응 #3787

반응 방정식

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

bromine

→

title compound

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

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the solvent was evaporated in vacuo
2. 2
   기타The residue was triturated with dichloromethane, which
3. 3
   기타was also evaporated in vacuo
4. 4
   기타to remove excess bromine
5. 5
   기타The residue was partitioned between dichloromethane/5% sodium bicarbonate (200 mL each)
6. 6
   기타The aqueous layer was separated
7. 7
   세척washed with dichloromethane
8. 8
   추출After extracting with dichloromethane (2×75 mL)
9. 9
   세척the combined organic layers were washed with water
10. 10
    건조dried (MgSO4)
11. 11
    여과filtered
12. 12
    기타evaporated in vacuo

실험 절차

A stirred, room temperature suspension of 5.3 g (10.0 mmol) of [S-(R*,R*)]-2-[2-[2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulfanyl benzoylamino]-3-methylpentanoic acid (prepared by the general method of Example 5) in 200 mL of dichloromethane was treated dropwise with 2.4 g (15.0 mmol) of liquid bromine. The reaction mixture was stirred at room temperature for 2 hours, and the solvent was evaporated in vacuo. The residue was triturated with dichloromethane, which was also evaporated in vacuo to remove excess bromine. The residue was partitioned between dichloromethane/5% sodium bicarbonate (200 mL each). The aqueous layer was separated, washed with dichloromethane, and acidified to pH 1.5 with 6.0M hydrochloric acid. After extracting with dichloromethane (2×75 mL), the combined organic layers were washed with water, dried (MgSO4), filtered and evaporated in vacuo to give 4.8 g of the title compound, mp 50°-52° C.

출처