Hydrochloric Acid → HCID 22010137, Verbindung

HRID 322901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322901
[C:1]([C:3]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:4]=1[O:5][CH:6]([C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])#[N:2].[OH-].[Na+].Cl>CO>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[CH:6]([O:5][C:4]1[CH:22]=[C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH:24]=[CH:25][C:3]=1[C:1]#[N:2])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53775193HCID 53775193, Verbindung

Produkt 1

HCID 22010137HCID 22010137, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2-chloro-6-fluorophenyl)butanoate (360 mg) in methanol (10 mL) containing 1 N sodium hydroxide (3 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is poured into 0.5 N HCl (20 mL) and extracted twice with ethyl acetate (20 mL). The combined organic phases are washed with brine (20 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a dark yellow oil. Crystallisation from a mixture of cyclohexane and ethyl acetate gives (RS)-4-(2-chloro-6-fluorophenyl)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-butanoic acid (210 mg) in the form of a beige solid, m.p. 128-130° C.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate (20 mL)
  2. washThe combined organic phases are washed with brine (20 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto leave a dark yellow oil
  7. customCrystallisation
  8. additionfrom a mixture of cyclohexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-26744bcc565e452db3dc79c9f745de38
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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