Hydrochloric Acid → HCID 178519974, Verbindung

HRID 2169481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169481
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]1[CH2:43][CH2:42]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[CH:41]1([N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:43][CH2:42]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 178455281HCID 178455281, Verbindung

Produkt 1

HCID 178519974HCID 178519974, VerbindungAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (450) (120 mg, 0.199 mmol) of in tetrahydrofuran (6 mL), was added 1N aqueous HCl (1.5 mL) and stirring was continued for 1 h at room temperature. After completion of the reaction, volatiles were removed and the residue was diluted with water (10 mL) and the pH was adjusted to pH 8 by using NaHCO3 and the mixture extracted with ethyl acetate (2×30 mL). The combined extracts were dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 50-60% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacidcyclopropyl-(2-hydroxyethyl)-amide (451) (80 mg, 82%) as a colorless gummy liquid.

Aufarbeitung

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue was diluted with water (10 mL)
  4. extractionthe mixture extracted with ethyl acetate (2×30 mL)
  5. customThe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1488f9299c104baaa19122d442f4650e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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