Carbamimidic acid, N,N'-bis(1-methylethyl)-, 1-methylethyl ester → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 464449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464449
[CH:1](OC(=NC(C)C)NC(C)C)([CH3:3])[CH3:2].[CH3:14][C:15]1([CH3:30])[C@@H:17](/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21])[C@H:16]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C(OCC)(=O)C>[CH3:14][C:15]1([CH3:30])[C@@H:17](/[CH:18]=[CH:19]\[C:20]([O:22][CH:1]([CH3:3])[CH3:2])=[O:21])[C@H:16]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Komponenten

4

Edukt 2

HCID 11332901Carbamimidic acid, N,N'-bis(1-methylethyl)-, 1-methylethyl esterHCID 12807775tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylate

Produkt 1

HCID 86739004tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2 g of O-isopropyl-N,N'-diisopropyl-isourea were added to a mixture of 2.7 g of the product of Step A and 10 ml of ethyl acetate and the mixture was stirred at room temperature for one hour, refluxed for 90 minutes and then cooled to 20° C. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The 3.5 g of oil residue were chromatographed over silica gel and eluted with a 7-3 benzene-cyclohexane mixture to obtain 1 g of tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate which was used as is for the next step.

Aufarbeitung

  1. temperaturerefluxed for 90 minutes
  2. temperaturecooled to 20° C
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customThe 3.5 g of oil residue were chromatographed over silica gel
  6. washeluted with a 7-3 benzene-cyclohexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-b8b1581900384123aa92dcf9829164f4
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04547522

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