1,1'-Carbonyldiimidazole → HCID 59909802, Verbindung

HRID 2183018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183018
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:34][C:35]1[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41](=[N:43]O)[NH2:42])=[CH:37][CH:36]=1>ClCCl>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([O:39][CH2:40][C:41]2[N:43]=[C:9]([C@H:8]([CH2:12][CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[O:11][N:42]=2)=[CH:45][CH:46]=1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 535925(Z)-2-(4-chlorophenoxy)-N'-hydroxyacetimidamideHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

Produkt 1

HCID 59909802HCID 59909802, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (300 mg, 1.00 mmol) in dichloromethane (15 ml) was treated with 1,1′-carbonyldiimidazole (162 mg, 1.00 mmol) and the solution was stirred at room temperature for 2 hours. 2-(4-chlorophenoxy)-N′-hydroxyethanimidamide (U.S. Pat. No. 97-815671 970313) (197 mg, 0.98 mmol) was then added and the mixture was stirred for 17 hours. The solvent was removed under reduced pressure and the residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1) to afford the title compound as a colourless oil (220 mg).

Aufarbeitung

  1. addition97-815671 970313) (197 mg, 0.98 mmol) was then added
  2. stirringthe mixture was stirred for 17 hours
  3. customThe solvent was removed under reduced pressure
  4. temperaturethe residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours
  5. customThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1)

Quellen und Nachweise

ORD-Eintrag
ord-95af435a750240a1a406a8d30f5c8a19
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897306B2

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