Sodium Methoxide → HCID 178450806, Verbindung

HRID 2169313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169313
Cl.[C:2]1([C:8]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22](=[O:37])/[C:23](/O)=[C:24](\[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[C:25](O)=[O:26])([CH3:20])([CH3:19])[CH3:18].C[O-].[Na+]>CO>[C:17]([O:21][C:22]([C:23]1[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:25]([OH:26])[N:16]=[C:14]([CH2:13][C:8]2([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1)=[O:37])([CH3:20])([CH3:18])[CH3:19]

Komponenten

5

Edukt 3

HCID 10942334Sodium MethoxideHCID 867258072-(1-Phenyl-cyclopentyl)-acetamidine HCl saltHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

Produkt 1

HCID 178450806HCID 178450806, VerbindungAusbeute 23,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(1-phenyl-cyclopentyl)-acetamidine hydrochloride salt (281) (500 mg, 2.09 mmol) and (E)-3-benzyloxy-2-hydroxy-4-oxo-pent-2-enoic acid tert-butyl ester (4) (970 mg, 3.15 mmol) in methanol (10 mL) was added a sodium methoxide solution (25% in methanol) (1.4 mL, 6.29 mmol) at 0° C. and then the reaction mixture was allowed to warm slowly up to room temperature while stirring was continued for 16 h. After completion of the reaction, the reaction mixture was quenched with 1N HCl (5 mL) and the methanol was evaporated and water (20 mL) was added. The mixture was extracted with ethyl acetate (3×20 mL) and the phases separated. The organic part was dried and concentrated to get a crude product, which was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to obtain 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (282) (230 mg, 23.82%) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with 1N HCl (5 mL)
  3. customthe methanol was evaporated
  4. additionwater (20 mL) was added
  5. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  6. customthe phases separated
  7. customThe organic part was dried
  8. concentrationconcentrated
  9. customto get a crude product, which
  10. customwas purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0172f54395154f61b4bc059f53cd84e0
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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