Hydrochloric Acid → HCID 178519975, Verbindung

HRID 2169477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169477
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:41][CH:42]1[CH2:44][CH2:43]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:42]1([CH2:41][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])[CH2:44][CH2:43]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 178455250HCID 178455250, Verbindung

Produkt 1

HCID 178519975HCID 178519975, VerbindungAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (446) (200 mg, 0.325 mmol) of in tetrahydrofuran (10 mL) was added (1N) aqueous HCl (2 mL). The mixture was stirred for 1 h at room temperature. After completion of the reaction, volatiles were removed, the residue diluted with water (10 mL) and pH was adjusted to 8 using NaHCO3. The mixture was extracted with ethyl acetate (2×30 mL), and the organic part was 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-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (447) (123 mg, 75%) as a colorless gummy liquid.

Aufarbeitung

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue diluted with water (10 mL) and pH
  4. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  5. customthe organic part was 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-b41f40deaecd4ad3a9123eff218ca3cd
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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