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Triethylamine → 5-chloro-N-(Trans-2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide

HRID 2240851
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2240851
[CH3:1][C:2]1([CH3:12])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[NH2:11].C(N(CC)CC)C.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26](O)=[O:27].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26]([NH:11][C@H:3]1[C@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1([CH3:12])[CH3:1])=[O:27]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68583334trans-2,2-Dimethyl-3-phenyl-cyclopropylamine

Produkt 1

HCID 576527575-chloro-N-(Trans-2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of trans-2,2-dimethyl-3-phenyl-cyclopropylamine (1.04 g, 6.5 mmol) in DCM was added triethylamine (1.435 g, 14.3 mmol), followed by 5-chloro-2-methoxybenzoic acid (1.446 g, 7.44 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (2.696 g, 8.45 mmol). The resulting mixture was stirred at room temperature overnight, then poured into water and extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (0% to 15% of EtOAc in hexane) to give 1.71 g (86% yield) of trans-5-chloro-N-(2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide, MS=330 [M+H]+.

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (0% to 15% of EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-54420dd2c7a14706af85b64cb95479a4
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723391B2

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