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4-Butoxybenzoic acid → HCID 11524913, Verbindung

HRID 1695522
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695522
[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)C(C)C)C.[C@H:32]1([CH2:42][O:43][C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[C@@H:41]2[N:36]([CH2:37][CH2:38][CH2:39][CH2:40]2)[CH2:35][CH2:34][CH2:33]1.[CH2:51]([O:55][C:56]1[CH:64]=[CH:63][C:59]([C:60](O)=[O:61])=[CH:58][CH:57]=1)[CH2:52][CH2:53][CH3:54]>CN(C=O)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH2:51]([O:55][C:56]1[CH:57]=[CH:58][C:59]([C:60]([NH:50][C:47]2[CH:48]=[CH:49][C:44]([O:43][CH2:42][C@H:32]3[C@@H:41]4[N:36]([CH2:37][CH2:38][CH2:39][CH2:40]4)[CH2:35][CH2:34][CH2:33]3)=[CH:45][CH:46]=2)=[O:61])=[CH:63][CH:64]=1)[CH2:52][CH2:53][CH3:54]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 729714-Butoxybenzoic acidHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66879100HCID 66879100, Verbindung

Produkt 1

HCID 11524913HCID 11524913, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

TOTU (78 mg) and ethyldiisopropylamine (31 mg), followed by 4-[(1R,9aR)-1-(octahydroquinolizin-1-yl)methoxy]phenylamine (62 mg), were added to a solution of 4-butoxybenzoic acid (46.4 mg) in DMF (2 ml) at 0° C. After a reaction time of three hours at room temperature, the mixture was diluted with sodium bicarbonate solution and ethyl acetate. After separation of the phases, the aqueous phase was extracted with ethyl acetate, and the combined organic phases were dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 436.60 (C27H36N2O3); MS (ESI): 437 (M+H+) was obtained in this way.

Aufarbeitung

  1. customAfter separation of the phases
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC
  6. customMS (ESI): 437 (M+H+) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-fc6fa48afc054918a731041046f8dafe
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163741B2

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