Cyclohexylamine → ent-Kaur-16-en-19-oic acid

HRID 1094475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094475
[CH3:1][C@:2]12[C@@H:11]3[CH2:12][CH2:13][C@@H:14]4[C:16]([CH2:18][C@@:10]3([CH2:15]4)[CH2:9][CH2:8][C@@H:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2)=[CH2:17].C(Cl)(C(Cl)=O)=O.[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C=O)C>[CH:29]1([NH-:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH3:1][C@:2]12[C@@H:11]3[CH2:12][CH2:13][C@@H:14]4[C:16]([CH2:18][C@@:10]3([CH2:15]4)[CH2:9][CH2:8][C@@H:7]1[C@@:6]([C:20]([OH:22])=[O:21])([CH3:19])[CH2:5][CH2:4][CH2:3]2)=[CH2:17]

Komponenten

7

Edukt 3

HCID 7965CyclohexylamineHCID 65578Oxalyl chlorideHCID 3034087ent-Kaur-16-en-19-oic acid

Produkt 2

HCID 3034087ent-Kaur-16-en-19-oic acidHCID 19097440HCID 19097440, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Kaurenoic acid can be dissolved in dry CH2Cl2 and treated with 10 equivalents of (COCl)2 followed by two drops of DMF. When the reaction stops bubbling, the CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum and the reaction residue can be redissolved in dry benzene and then treated with 5 equivalents of cyclohexylamine to yield N-cyclohexylamide derivative of kaurenoic acid.

Aufarbeitung

  1. customWhen the reaction stops bubbling
  2. customthe CH2Cl2 solvent and (COCl)2 can be evaporated under vacuum
  3. dissolutionthe reaction residue can be redissolved in dry benzene

Quellen und Nachweise

ORD-Eintrag
ord-1ccb86fc64b94d81ae056aaeecf7bd78
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133915B2

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