1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(3-[(5s)-5-(Acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-3-yl]oxy-3-oxopropyl)benzoic acid

HRID 720947

Reaktionsgleichung

Reaktionsgleichung von HRID 720947
[CH3:1][C:2]([NH:4][CH:5]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[C:13]2[C:8](=[CH:9][C:10]([O:25][CH3:26])=[C:11]([O:23][CH3:24])[C:12]=2[O:21][CH3:22])[CH2:7][CH2:6]1)=[O:3].CCN=C=NCCCN(C)C.[C:38]([C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49](O)=[O:50])=[CH:43][CH:42]=1)([OH:40])=[O:39]>CN(C1C=CN=CC=1)C>[C:2]([NH:4][C@@H:5]1[C:15]2[CH:16]=[C:17]([O:20][C:49](=[O:50])[CH2:48][CH2:47][C:44]3[CH:45]=[CH:46][C:41]([C:38]([OH:40])=[O:39])=[CH:42][CH:43]=3)[CH:18]=[CH:19][C:14]=2[C:13]2[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 97865N-AcetylcolchicinolHCID 8540543-(4-Carboxyphenyl)propionic Acid

Produkt 1

HCID 98285094-(3-[(5s)-5-(Acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-3-yl]oxy-3-oxopropyl)benzoic acidAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

A solution of N-acetyl-colchicinol (0.357 g; 1 mmol), EDCI (0.23 g; 1.2 mmol), DMAP (0.025 g; 0.2 mmol) and 3-(4-carboxyphenyl)propionic acid (0.233 g; 1.2 mmol) was stirred at ambient temperature overnight. After removal of the solvent by evaporation, the residue was purified by preparative HPLC on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l pH7) (50/50) to give 4-(3-[(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl]oxy-3-oxopropyl)benzoic acid.

Aufarbeitung

  1. customAfter removal of the solvent
  2. customby evaporation
  3. customthe residue was purified by preparative HPLC on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l pH7) (50/50)

Quellen und Nachweise

ORD-Eintrag
ord-32a15131e0bb4dd5b43db80ce2dbe2e1
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135502B1

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