Hydrochloric Acid → HCID 22010157, Verbindung

HRID 322903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322903
[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[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])#[N:2].[OH-].[Na+].Cl>CO>[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[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53853519HCID 53853519, Verbindung

Produkt 1

HCID 22010157HCID 22010157, VerbindungAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2,5-dimethylphenyl)butanoate (500 mg) in methanol (20 mL) containing 1 N sodium hydroxide (5 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is poured into 0.5 N HCl (20 mL) and extracted three times 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 brown oil. Crystallisation with cyclohexane gives (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2,5-dimethylphenyl) butanoic acid, (170 mg) in the form of an off-white solid, m.p. 135-136° C. [Elemental analysis:- C,68.4, H, 5.46, N, 3.33%. Calculated:- C,68.7, H, 5.57, N, 3.00%]

Aufarbeitung

  1. extractionextracted three times 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 brown oil
  7. customCrystallisation with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-ab089bd6db09404da5237e326f867a10
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

Notizen zur Reaktion

Wird geladen…