Pyridine → HCID 178496221, Verbindung

HRID 53463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53463
[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15](O)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.S(Cl)(Cl)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:45][C@@H:46]1[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:53])[CH2:48][CH2:47]1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O.O>[C:1]([O:5][C:6](/[C:8](/[CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:9]/[C:10]1([C:15]([NH:45][C@@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]([O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[O:53])[CH2:48][CH2:47]2)=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 1049PyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11069968(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acidHCID 178427656HCID 178427656, Verbindung

Produkt 1

HCID 178496221HCID 178496221, VerbindungAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of (E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid (1.0 g, 3.04 mmol) in ethyl acetate (10.6 mL) under a nitrogen atmosphere at room temperature was added dimethylformamide (1 drop), pyridine (0.49 mL, 6.08 mmol) and thionyl chloride (0.28 mL, 3.95 mmol) and the mixture stirred at room temperature for 40 minutes. Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate (1.29 g, 3.19 mmol) was added at room temperature followed by triethylamine (1.27 mL, 9.12 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with distilled water (50 mL) and ethyl acetate (50 mL) and the layers separated. The ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.552 g). The crude product was purified by chromatography on silica by elution with hexane/ethyl acetate (1:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil (1.07 g, 65%).

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. customthe layers separated
  3. washThe ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd5674891c5140d7b096a8298f271e93
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618970

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