Dichloromethane → HCID 69629012, Verbindung

HRID 987317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987317
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[C:31]([C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32].ClCCl>O1CCCC1.CO.ClCCl>[C:31]([C:35]1[CH:36]=[CH:37][C:38]([C:39]([NH:2][C:3]2[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=3)=[CH:7][CH:8]=2)=[O:40])=[CH:42][CH:43]=1)([CH3:34])([CH3:32])[CH3:33]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 743724-tert-Butylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 86595065HCID 86595065, Verbindung

Produkt 1

HCID 69629012HCID 69629012, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (described in Example 56a) (0.2 g; 0.547 mmole) was dissolved in tetrahydrofurane (5 ml). Sodium hydrogencarbonate (0.053 g; 0.631 mmole) was added and the mixture was stirred for a little while. 4-tert-Butylbenzoyl chloride (0.118 g; 0.6 mmole) was added. The reaction mixture was stirred overnight and then evaporated to dryness. Dichloromethane and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography of the residue on silica gel(Isolute, SI) using dichloromethane:heptane (1:1), then dichloromethane and finally methanol: dichloromethane (1:99) as eluants gave 0.238 g (89% yield) of 3-{4-[2-{4-(4-[tert-butyl]benzoyl)aminophenyl}ethoxy]phenyl}-2-(S)-ethoxypropanoic acid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight
  2. customevaporated to dryness
  3. additionDichloromethane and water were added to the residue
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4ed22c6e7b2845df8c13de7ac21117c0
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

Notizen zur Reaktion

Wird geladen…