1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57847051, Verbindung

HRID 550304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550304
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]2[NH:12][CH2:13][CH2:14][CH:4]2[CH:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]([NH:29][C@@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@@H:31]1[C:36](O)=[O:37])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(#N)C>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C@@H:5]2[N:12]([C:36]([C@H:31]3[CH2:32][CH2:33][CH2:34][CH2:35][C@H:30]3[NH:29][C:21](=[O:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:37])[CH2:13][CH2:14][C@@H:4]2[C@@H:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 671504335-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline

Produkt 1

HCID 57847051HCID 57847051, VerbindungAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 5-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (130 mg, 0.48 mmol), (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (131 mg, 0.53 mmol), WSC (116 mg, 0.61 mmol), HOBt (97 mg, 0.63 mmol), acetonitrile (5 ml) and tetrahydrofuran (5 ml) was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous Na2SO4), and the solvent was evaporated. The residue was subjected to column chromatography using silica gel (150 g) and eluted with hexane-ethyl acetate (4:1-1:1, v/v) to give the title compound (200 mg, 84%) as an amorphous form.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (over anhydrous Na2SO4)
  4. customthe solvent was evaporated
  5. washeluted with hexane-ethyl acetate (4:1-1:1

Quellen und Nachweise

ORD-Eintrag
ord-e4542a682baa46eb9ea8eb1632ed6ba0
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943770B2

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