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Diisopropylethylamine → HCID 24785365, Verbindung

HRID 2244375
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2244375
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH:15]1([C:20]2[CH:39]=[CH:38][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:10]=1)[C:7]([N:25]([CH2:24][C:23]1[CH:22]=[CH:21][C:20]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:39][CH:38]=1)[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=1)=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13064663HCID 13064663, VerbindungHCID 25180023HCID 25180023, Verbindung

Produkt 1

HCID 24785365HCID 24785365, VerbindungAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 50 mg of 5-chloro-2-isopropylamino-benzoic acid (0.23 mmol) and 81 mg (0.23 mmol) of (4-cyclopentyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 4 ml of DMF were added 75 mg of TBTU (0.23 mmol) and 0.2 ml (1.17 mmol) of N,N-di-isopropylethyl amine. After stirring the reaction mixture over night at RT it was diluted with 50 ml water and extracted with ethyl acetate. The combined organic phases were washed with 10%-aqueous KHCO3 solution, 0.1M HCl solution and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining oil was purified by column chromatography (silica gel; heptane 100% to heptane/EtOAc 4:1) to give 90 mg (71%) of a colorless oil. MS (ISP) 543.5 (M+H)+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with 10%-aqueous KHCO3 solution, 0.1M HCl solution and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe remaining oil was purified by column chromatography (silica gel; heptane 100% to heptane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4d5a6c8075484f158f4bf63a8c69ad5b
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678818B2

Notizen zur Reaktion

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