Citric Acid → HCID 19735035, Verbindung

HRID 326720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326720
[C:1]([CH:3]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[OH:26].CCN=C=NCCCN(C)C.Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:1]([CH:3]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:4]([O:6][CH2:18][CH3:19])=[O:5])#[N:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[O:26][C:4](=[O:5])[CH:3]([C:1]#[N:2])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 72712,4,5-TrichlorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19735046HCID 19735046, Verbindung

Produkt 2

HCID 19735035HCID 19735035, VerbindungHCID 53675740HCID 53675740, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Cyano-3-(3-indolyl)propionic acid from Step a, 2,4,5-trichlorophenol (394 mg, 2 mmol) and EDCl (392 mg, 2 mmol) were combined in methylene chloride (10 mL) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was added to 20 mL of 10% citric acid solution and the aqueous mixture was extracted with methylene chloride. The methylene chloride was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1:4 to 1:2) to give 210 mg (37% yield from ethyl 2-cyano-3-(3-indolyl)propionate) of the title compound.

Aufarbeitung

  1. extractionthe aqueous mixture was extracted with methylene chloride
  2. customThe methylene chloride was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1:4 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-463fe5aa312b4a6d9030c9e0a7bb87e9
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270302

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