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Water → N-{(1R,2S)-2-[(3aR*,4R*,9bR*)-(5-Acetyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl)carbonyl]cyclohexyl}benzamide

HRID 550311
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 550311
[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:44](Cl)(=[O:46])[CH3:45].O>C(Cl)(Cl)Cl>[C:44]([N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C@@H:15]2[N:19]([C:20]([C@H:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]3[NH:28][C:29](=[O:36])[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:21])[CH2:18][CH2:17][C@H:16]2[C@@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:46])[CH3:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57846915HCID 57846915, Verbindung

Produkt 1

HCID 68981617N-{(1R,2S)-2-[(3aR*,4R*,9bR*)-(5-Acetyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl)carbonyl]cyclohexyl}benzamideAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

The compound (130 mg, 0.27 mmol) of Example 1 and triethylamine (69 mg, 0.30 mmol) were dissolved in chloroform (2 ml), acetyl chloride (99 mg, 0.33 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hr. and at 60° C. for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated. The residue was subjected to column chromatography using silica gel (150 g), and eluted with hexane-ethyl acetate (3:1-0:1, v/v) to give the title compound (65 mg, 46%) as an amorphous form.

Aufarbeitung

  1. temperaturecooling
  2. waitand at 60° C. for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried (over anhydrous MgSO4)
  6. customthe solvent was evaporated
  7. washeluted with hexane-ethyl acetate (3:1-0:1

Quellen und Nachweise

ORD-Eintrag
ord-ea96d154682b4cceb414abd0a324b65e
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07943770B2

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