Triethylamine → n-[(5s)-3-Phenoxycarbonyloxy-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl]acetamide

HRID 720952

Reaktionsgleichung

Reaktionsgleichung von HRID 720952
[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].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29].C(N(CC)CC)C>ClCCl>[O:30]([C:28]([O:20][C:17]1[CH:18]=[CH:19][C:14]2[C:13]3[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=3[CH2:7][CH2:6][C@H:5]([NH:4][C:2](=[O:3])[CH3:1])[C:15]=2[CH:16]=1)=[O:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 97865N-Acetylcolchicinol

Produkt 1

HCID 57245389n-[(5s)-3-Phenoxycarbonyloxy-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl]acetamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-acetyl colchicinol (0.35 g; 0.98 mmol), phenyl chloroformate (145 μl; 1.08 mmol) and triethylamine (150 μl; 1.08 mmol) in dichloromethane (20 ml) was stirred at ambient temperature for 1 hour. The mixture was washed with water and the organic phase evaporated. The residue was purified by flash chromatography, eluting with ethyl acetate/petroleum ether (80/20) to give N-[(5S)-3-phenoxycarbonyloxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide as a foam.

Aufarbeitung

  1. washThe mixture was washed with water
  2. customthe organic phase evaporated
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate/petroleum ether (80/20)

Quellen und Nachweise

ORD-Eintrag
ord-a04e91f8222b40ecae8999e9735ae656
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135502B1

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