Methanol → 5-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 1349475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1349475
[CH2:1]([O:8][C:9]1[C:10](=[O:36])[C:11]([C:32]([O:34]C)=[O:33])=[CH:12][N:13]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:36])[C:11]([C:32]([OH:34])=[O:33])=[CH:12][N:13]([CH2:26][CH:27]([O:28][CH3:29])[O:30][CH3:31])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 23077726Methyl 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Produkt 1

HCID 230776405-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acidAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of methyl 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (2.0 g) in tetrahydrofuran (20 ml)-methanol (10 ml) was added 4N aqueous lithium hydroxide solution (1.5 ml) and the mixture was stirred at 70° C. for 1 hr. The precipitated solid was removed by thin layer of celite and washed with methanol. The solvent was evaporated and 1N aqueous hydrochloric acid (6.5 ml) and water (50 ml) were added. The mixture was extracted twice with ethyl acetate (75 ml each). The ethyl acetate layer was dried, concentrated and crystallized from ethyl acetate-diisopropyl ether to give 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (1.2 g).

Aufarbeitung

  1. customThe precipitated solid was removed by thin layer of celite
  2. washwashed with methanol
  3. customThe solvent was evaporated
  4. addition1N aqueous hydrochloric acid (6.5 ml) and water (50 ml) were added
  5. extractionThe mixture was extracted twice with ethyl acetate (75 ml each)
  6. dry with materialThe ethyl acetate layer was dried
  7. concentrationconcentrated
  8. customcrystallized from ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-befb68c3e0134c0b9cf6bfc7617158eb
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211572B2

Notizen zur Reaktion

Wird geladen…