Lithium Hydroxide → HCID 86595065, Verbindung

HRID 987295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987295
[ClH:1].C([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)C.[OH-].[Li+]>O1CCCC1.O>[ClH:1].[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][C@H:6]([O:24][CH2:25][CH3:26])[C:5]([OH:27])=[O:4])=[CH:9][CH:10]=2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86595066HCID 86595066, Verbindung

Produkt 1

HCID 86595065HCID 86595065, VerbindungAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Water (200 ml) was added to a solution of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (described in Example 41b) (15 g; 42 mmole) in tetrahydrofuran (100 ml). Lithium hydroxide (3.4 g; 84 mmole) dissolved in a small amount of water was added while stirring and then the reaction mixture was stirred at room temperature over night. Tetrahydrofuran was evaporated and the remaining residue was extracted twice with ethyl acetate. The water phase was acidified with hydrochloric acid (2 M) and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate. Evaporation gave 6.4 g of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride. The acidic water phase, from above, was neutralized with sodium hydroxide to pH5 and extracted with dichloromethane. The organic phase was dried with magnesium sulfate and evaporated. This procedure gave 1.4 g more of the desired product. The total yield of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride was 7.8 g (50.8%).

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature over night
  3. customTetrahydrofuran was evaporated
  4. extractionthe remaining residue was extracted twice with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-cc444ba008414a1fb08ad4195cafa932
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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