Реакция #1606849

Уравнение реакции

N,N2,O-trimethyl-3-oxoserinamide hydrochloride

Intermediate 5-2

N,N2,O-trimethyl-3-oxoserinamide hydrochloride

HATU

DIPEA

4′-((t-butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acid

→

4-((t-butoxycarbonyl)(methyl)amino)-4′-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl

Выход 51.0%

Растворители

DMF

water

Ethyl acetate

Условия реакции

Обработка

1. 1
   Другоеto isolate the organic layer
2. 2
   Промывкаthe extract was washed sequentially with water and brine
3. 3
   СушкаThe system was dried over anhydrous sodium sulfate
4. 4
   Другоеafter separation of the
5. 5
   Фильтрацияdesiccant by filtration
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   ДругоеThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

Методика

N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 90 mg), HATU (0.17 g) and DIPEA (0.16 mL) were added to a DMF (2.0 mL) solution of 4′-((t-butoxycarbonyl)(methyl)amino)biphenyl-4-carboxylic acid (0.10 g), as obtained in Example 2-(2), and the mixture was stirred for 16 hours at room temperature. Ethyl acetate and water were added to the reaction mixture to isolate the organic layer, and the extract was washed sequentially with water and brine. The system was dried over anhydrous sodium sulfate and, after separation of the desiccant by filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to obtain 4-((t-butoxycarbonyl)(methyl)amino)-4′-(((2-methoxy-1-((methylamino)carbonyl)-2-oxoethyl)(methyl)amino)carbonyl)biphenyl (white foam) (73 mg, 51%).

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