Sodium Hydroxide → 4-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acid

HRID 1267425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267425
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH:21]([OH:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[OH:29][CH:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:20][CH2:19][CH:14]1[CH2:15][CH2:16][C:17](=[O:18])[N:13]1[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 129700864-{3-[2-(3-Hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester

Produkt 1

HCID 113268964-(3-(2-(3-Hydroxy-4-phenylbutyl)-5-oxopyrrolidin-1-yl)propyl)benzoic acidAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-{3-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester (2.28 g, 5.57 mmol) in MeOH (20 mL) was added 2N NaOH (5 mL). The reaction mixture was stirred at room temperature for 20 h and was heated under reflux for 3 h. The volatiles were removed in vacuo and the residue was diluted with CH2Cl2 and 1 N HCl. The aqueous solution was extracted with CH2Cl2 (2×) and the combined organic extracts were washed with brine. The organic solution was dried (MgSO4), filtered and concentrated to yield the title compound (2.03 g). 1H NMR (CDCl3) δ7.98 (d, 2H), 7.34-7.18 (m, 7H), 3.80 (m, 1H), 3.67 (m, 1H), 3.58 (m, 1H), 2.97 (m, 1H), 2.81 (m, 1H), 2.68 (m, 3H), 2.45-2.27 (m, 2H), 2.13-1.30 (m, 9H); MS 396.3 (M+1), 394.2 (M−1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe volatiles were removed in vacuo
  4. additionthe residue was diluted with CH2Cl2 and 1 N HCl
  5. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialThe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ffd681022fe34790ba054512fbf34caa
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552067B2

Notizen zur Reaktion

Wird geladen…