Pyridine → 3-[4-(3-Thienyl)phenyl]alanine

HRID 1957025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957025
C([O:5][C:6](=[O:17])[C@H:7](C)[N:8]=CC1C=CC=CC=1)(C)(C)C.[S:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=2)=[CH:19]1.N1C=CC=CC=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[S:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C@@H:7]([C:6]([OH:17])=[O:5])[NH2:8])=[CH:25][CH:24]=2)=[CH:19]1

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 13433755Tert-butyl N-benzylidenealaninateHCID 137735383-(4-(Bromomethyl)phenyl)thiophene

Produkt 1

HCID 537748243-[4-(3-Thienyl)phenyl]alanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(phenylmethylene)alanine t-butyl ester (210 mg, 0.90 mmol), 4-(3-thienyl)phenylmethyl bromide (250 mg, 0.99 mmol), and pyridine (7 ml, 0.09 mmol) in methylene chloride (1.8 ml) are added potassium hydroxide (505 mg, 9.0 mmol) and potassium carbonate (1.24 g, 9.0 mmol). The mixture is stirred at room temperature for 2 days, then filtered and washed with methylene chloride. The filtrate and washings are concentrated in vacuo to give a crude 3-[4-(3-thienyl)phenyl]alanine as a yellow oil.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with methylene chloride
  3. concentrationThe filtrate and washings are concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-694e4a723e3a458da868e81014436c64
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780498

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