反应详情

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.

1. customthe solvent was evaporated in vacuo
2. customThe residue was triturated with dichloromethane, which
3. customwas also evaporated in vacuo
4. customto remove excess bromine
5. customThe residue was partitioned between dichloromethane/5% sodium bicarbonate (200 mL each)
6. customThe aqueous layer was separated
7. washwashed with dichloromethane
8. extractionAfter extracting with dichloromethane (2×75 mL)
9. washthe combined organic layers were washed with water
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customevaporated in vacuo