Acetonitrile → (R)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acid

HRID 1018830

Reaktionsgleichung

Reaktionsgleichung von HRID 1018830
Cl.[NH2:2][C@H:3]([CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:4]([OH:6])=[O:5].[C:14](#N)[CH3:15]>>[CH:8]1([CH2:7][C@@H:3]([N:2]2[CH2:15][C:14]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:5])[C:4]([OH:6])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

3

Edukt 2

HCID 6342AcetonitrileHCID 56777007(R)-2-Amino-3-cyclohexylpropanoic acid hydrochloride

Produkt 1

HCID 1477120(R)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acidAusbeute 63 %

Versuchsvorschrift

A mixture of (R)-(+)-α-aminocyclohexanepropionic acid hydrochloride (2.69 g; 15.7 mmol) and phthalic dicarboxaldehyde (2.50 g; 14.6 mmol) in acetonitrile (60 mL) was refluxed for 42 h under nitrogen. The mixture was allowed to cool to room temperature and further cooled to 0° C. The solid was filtered off and washed once with cold acetonitrile to give 2.65 g (63%) of (R)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid as a white solid: EI-HRMS m/e calcd for C17H21NO3 (M+) 287.1521, found 287.1523.

Aufarbeitung

  1. temperaturewas refluxed for 42 h under nitrogen
  2. temperaturefurther cooled to 0° C
  3. filtrationThe solid was filtered off
  4. washwashed once with cold acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-737d911fb49b4d2599d44c4c7ee0aaa1
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482951B2

Verknüpfte Notizen

Wird geladen…