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Diethyl Pyrocarbonate → HCID 57847036, Verbindung

HRID 1009934
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009934
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@H:18]3[CH2:19][CH2:20][NH:21][C@H:17]3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10]2)=[CH:5][CH:4]=1.[C:22]([NH:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]1[C:37](O)=[O:38])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@H:18]3[CH2:19][CH2:20][N:21]([C:37]([C@H:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]4[NH:30][C:22](=[O:29])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:38])[C@H:17]3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10]2)=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 67150531HCID 67150531, Verbindung

Produkt 1

HCID 57847036HCID 57847036, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a suspension of (3aS,4R,9bR)-4-[4-(methylthio)phenyl]-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (1.10 g, 3.0 mmol) and (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (0.74 g, 3.0 mmol) in DMF (20 ml) were added under ice-cooling, triethylamine (0.91 g, 9.0 mmol), and then a solution of DEPC (0.49 g, 3.0 mmol) in DMF (5 ml). The reaction mixture was stirred at room temperature for 16 hrs., the reaction mixture was poured into ice water and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (2:1-1:1, v/v) to give N-[(1R,2S)-2-({(3aR,4R,9bR)-4-[4-(methylthio)phenyl]-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl}carbonyl)cyclohexyl]benzamide (0.45 g, 29%) from the first eluted fraction.

Aufarbeitung

  1. additionwere added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washeluted with hexane-ethyl acetate (2:1-1:1

Quellen und Nachweise

ORD-Eintrag
ord-1c1f94b0b2c44782aa170805a51d5d36
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973163B2

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