Water → 5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamide

HRID 2202335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202335
[NH2:1][CH:2]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][CH3:26])=[CH:20][CH:19]=1)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[C:8]([F:17])[CH:7]=1)=[O:4].[F:27][B:28]([F:56])[N:29]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[C:30]1/[CH:36]=[C:37]1\[N:38]=[C:39]([CH2:42][CH2:43][CH2:44][CH2:45][C:46](ON2C(=O)CCC2=O)=[O:47])[CH:40]=[CH:41]\1.O.O.C(#N)C>CN(C=O)C>[F:56][B:28]([F:27])[N:29]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[C:30]1/[CH:36]=[C:37]1\[N:38]=[C:39]([CH2:42][CH2:43][CH2:44][CH2:45][C:46]([NH:1][CH:2]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][O:25][CH3:26])=[CH:22][CH:23]=2)[C:3]([NH:5][C:6]2[CH:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:14])([CH3:15])[CH3:16])=[C:8]([F:17])[CH:7]=2)=[O:4])=[O:47])[CH:40]=[CH:41]\1

Komponenten

6

Edukt 4

HCID 962WaterHCID 103646301-((5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)pentanoyl)oxy)pyrrolidine-2,5-dioneHCID 18373917Acetonitrile--water (1/1)HCID 1317357652-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl) acetamide

Produkt 1

HCID 1317357665-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamideAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the crude 2-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl)acetamide (9.07 mg, 0.02 mmol) in DMF (0.5 mL) was added 1-((5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)pentanoyl)oxy)pyrrolidine-2,5-dione (BODIPY (registered trademark) FL-C5 succinimidyl ester) (5.0 mg, 0.01 mmol) at room temperature, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane), and then preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)) to give 5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamide (3.8 mg, 5.58 μmol, 46.6%) as an orange solid, which is a fluorescent-labeled synthetic ligand.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-241b26c5805c4fc692e8b5a386553aa5
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365520B2

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