Sodium Hydroxide → 3-Acetyl-4-(2-isopropylphenyl)-6-methyl-1-carboxymethyl-2-pyridinone

HRID 398376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398376
[C:1]([C:4]1[C:5](=[O:26])[N:6]([CH2:20][C:21]([O:23]CC)=[O:22])[C:7]([CH3:19])=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:18])[CH3:17])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[C:5](=[O:26])[N:6]([CH2:20][C:21]([OH:23])=[O:22])[C:7]([CH3:19])=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:18])[CH3:17])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 230001623-Acetyl-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone

Produkt 1

HCID 230001833-Acetyl-4-(2-isopropylphenyl)-6-methyl-1-carboxymethyl-2-pyridinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-acetyl-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 3 of Example XX (0.20 g, 0.56 mmol) in ethanol (4 mL) was added aqueous NaOH (0.62 mL of a 1.0 N solution, 0.62 mmol). The resulting solution was stirred at ambient temperature for 2 h and the solvent was removed in vacuo. The residue was partitioned between EtOAc and 1.0 N aqueous HCl. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (HPLC RT=18.11 min, method B).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1.0 N aqueous HCl
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bdd5c6c64fa04af9a393582da96f25e1
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610692B1

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