Water → HCID 178524875, Verbindung

HRID 2169250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169250
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 178450815HCID 178450815, Verbindung

Produkt 1

HCID 178524875HCID 178524875, VerbindungAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred solution of 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.0 g, 3.788 mmol) in tetrahydrofuran-H2O (2:1) (30 mL) Li(OH).H2O (1.591 g, 37.88 mmol) was added, then the reaction mixture was stirred under reflux for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.1). After completion of the reaction, volatiles were removed, the reaction mixture was diluted with water, the pH was adjusted to pH ˜7 with 1N HCl, then the reaction mixture was extracted with ethyl acetate. The organic part was dried with Na2SO4, then concentrated to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (205) (1.3 g, 72.5%) as a white solid.

Aufarbeitung

  1. temperatureunder reflux for 16 h
  2. customAfter completion of the reaction, volatiles
  3. customwere removed
  4. additionthe reaction mixture was diluted with water
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe organic part was dried with Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8c86fbbb53594578a26687c84a81775b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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