Реакция #53600

Уравнение реакции

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

triethylamine

2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acid

phenylalanine tert butyl ester hydrochloride

→

(S)-2-({1-[2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazol-7-yl]-methanoyl}-amino)-3-phenylpropionic acid

Растворители

water

DMF

DMF

Условия реакции

Обработка

1. 1
   Другоеresulting in the formation of a tan precipitate
2. 2
   Фильтрацияthe mixture was filtered
3. 3
   Другоеto dry
4. 4
   workup.DISSOLUTIONdissolved in 90% trifluoroacetic acid (1 mL)
5. 5
   workup.STIRRINGThe solutions were agitated for 6 hrs
6. 6
   Концентрированиеthen concentrated under reduced pressure
7. 7
   Другоеsubjected to Gilson HPLC purification

Методика

To the 2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acid (0.05 g, 0.1 mmol) in DMF (0.5 mL) at room temperature was added phenylalanine tert butyl ester hydrochloride (0.11 mmol). A cocktail solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.021 g, 0.11 mmol), triethylamine (0.3 mmol) in DMF (0.5 mL) was added and the reaction was agitated at room temperature for 18 hours. 1 ml water was added to the reaction mixture resulting in the formation of a tan precipitate. the mixture was filtered and allowed to dry. The solid mass was transferred into vial and dissolved in 90% trifluoroacetic acid (1 mL). The solutions were agitated for 6 hrs then concentrated under reduced pressure. The residures were taked up in DMSO and subjected to Gilson HPLC purification. The title compound was abtained as solid.(0.006 g, 10%). MS(ES) m/z 556 [M+H].

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