Ethyl Acetate → HCID 178450815, Verbindung

HRID 2169249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169249
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[C:10]1([CH2:15][C:16]([NH2:18])=[NH:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:19]([O:23][C:24](=[O:39])/[C:25](/O)=[C:26](\[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)/[C:27](O)=[O:28])([CH3:22])([CH3:21])[CH3:20].C(OCC)(=O)C>CO.CCCCCC>[C:19]([O:23][C:24]([C:25]1[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:27]([OH:28])[N:18]=[C:16]([CH2:15][C:10]2([C:4]3[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:3]=3[Cl:2])[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:17]=1)=[O:39])([CH3:22])([CH3:20])[CH3:21]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 867258982-[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride

Produkt 1

HCID 178450815HCID 178450815, VerbindungAusbeute 53,55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[1-(2,5-dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride (2=3) (2.0, 7.407 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (3.422 g, 11.111 mmol) in methanol (50 mL) NaOMe (25% in methanol; 4.8 mL) was added dropwise at 0° C. and stirred at room temperature for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.6). The reaction mixture was quenched with HCl (1N; 5 mL), methanol was removed, the product was diluted with water and the mixture was extracted with ethyl acetate. The combined organic part was dried, the product was concentrated and the crude product was purified using a normal silica gel column using a gradient eluent of 10 to 40% ethyl acetate in hexane to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.1 g, 53.55%) as a yellow solid.

Aufarbeitung

  1. customThe reaction mixture was quenched with HCl (1N; 5 mL), methanol
  2. customwas removed
  3. additionthe product was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe combined organic part was dried
  6. concentrationthe product was concentrated
  7. customthe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-9208057309df4b7ab9ce11dc4a8ac5a6
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

Notizen zur Reaktion

Wird geladen…