Tetrahydrofuran → (E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)methyl)-8-oxo-6-octenoic acid

HRID 555358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555358
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:33])/[C:11](/[CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1.O.[OH-].[Li+].O1CCCC1>O>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:33])/[C:11](/[CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66986989methyl (E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)methyl)-8-oxo-6-octenoate

Produkt 1

HCID 66987029(E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)methyl)-8-oxo-6-octenoic acidAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl (E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)-methyl)-8-oxo-6-octenoate (350 mg, 0.77 mM) obtained in Example (2-1-1) was dissolved in water (1 ml), and lithium hydroxide monohydrate (LiOH.H2O) (96 mg, 2.31 mM) and tetrahydrofuran (4 ml) were added thereto. The resulting mixture was stirred at room temperature for 10 mins, followed by stirring at 50° C. for 3 hrs. After the completion of reaction, the reaction mixture was cooled to room temperature, followed by adding ice water thereto. Then, the solvent was removed under reduced pressure, and the residue was cooled to 5° C. again and acidified (pH 4) with 2N hydrochloric acid. The resultant was filtered and dried over anhydrous magnesium sulfate to obtain the 350 mg of the title compound as a white solid (yield 85%).

Aufarbeitung

  1. stirringby stirring at 50° C. for 3 hrs
  2. customAfter the completion of reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customThen, the solvent was removed under reduced pressure
  5. temperaturethe residue was cooled to 5° C. again
  6. filtrationThe resultant was filtered
  7. dry with materialdried over anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-1a19cfdb2c064a29a1e754558c60f281
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053435B2

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