Dicyclohexylcarbodiimide → HCID 53971898, Verbindung

HRID 726946

Reaktionsgleichung

Reaktionsgleichung von HRID 726946
[F:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=O)[CH2:3]1.[OH-].[K+].[Cl:12][C:13]1[C:18]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:17][C:16]([N:23]=[C:24]=[S:25])=[C:15]([F:26])[CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>CO.O.C(#N)C>[Cl:12][C:13]1[C:18]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:17][C:16]([N:23]=[C:24]2[N:5]3[CH2:6][CH:2]([F:1])[CH2:3][CH:4]3[C:7](=[O:9])[S:25]2)=[C:15]([F:26])[CH:14]=1

Komponenten

8

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 14797Potassium HydroxideHCID 136079331-Chloro-5-fluoro-4-isothiocyanato-2-[(propan-2-yl)oxy]benzeneHCID 222148884-Fluoro-L-proline

Produkt 1

HCID 53971898HCID 53971898, VerbindungAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1.31 g (0.01 mol) 4-fluoroproline, 30 mL 2N KOH in methanol and 10 mL water is prepared before 2.46 g (0.01 mol) 4-chloro-2-fluoro-5-isopropoxy-phenylisothiocyanate dissolved in 250 mL methanol is added dropwise. The reaction mixture is stirred overnight at room temperature, the aqueous phase adjusted to pH 2 and the resultant product (3.77 g, See Formula X) is filtered. The compound thus obtained is dissolved in 50 mL acetonitrile before 2.59 g (0.01 mol) dicyclohexylcarbodiimide is added at room temperature. The reaction mixture is stirred for 3 h and the crude product is purified by silica gel chromatography to give 3.24 g (85% yield) of the desired product.

Aufarbeitung

  1. additionis added dropwise
  2. filtrationthe resultant product (3.77 g, See Formula X) is filtered
  3. customThe compound thus obtained
  4. additionis added at room temperature
  5. stirringThe reaction mixture is stirred for 3 h
  6. customthe crude product is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-804654d342e24569ad4a9a350c28f6c9
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712225

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