1,2-Dichloroethane → HCID 178443268, Verbindung

HRID 735829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735829
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[NH:31][C:32](=[NH:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:32]([NH:44][O:26][C:25]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:29][CH:28]=1)=[O:27])(=[NH:31])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 671885994-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)-benzoic AcidHCID 178443266N'-hydroxydodecanimidamide

Produkt 1

HCID 178443268HCID 178443268, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)-benzoic acid (102 mg, 0.25 mmol), N-hydroxydodecanimidamide (70 mg, 0.33 mmol) and DMAP (3 mg, 0.03 mmol) in anhydrous DCM (15 mL) was added EDC (62 mg, 0.33 mmol) and the resulting reaction mixture was stirred at RT for 14 h. Evaporation of the solvents gave an oil. This crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 80/20) to give the title compound as a colorless oil (36 mg, 24%). 1H NMR (CDCl3, 300 MHz) δ 8.01 (d, J=8.1 Hz, 2H), 7.60 (d, J=8.1 Hz, 2H), 7.40-7.20 (m, 4H), 4.88 (br s, 2H), 4.51 (s, 2H), 4.42 (s, 2H), 2.36 (t, J=8.2 Hz, 2H), 1.75-1.59 (m, 2H), 1.49 (s, 9H), 1.45-1.16 (m, 16H), 0.89 (t, J=7.0 Hz, 3H). HPLC (Condition A), Rt: 5.42 min (HPLC purity: 96.1%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customEvaporation of the solvents
  3. customgave an oil
  4. customThis crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-3d861b7ed7a5412fa1471881905def9b
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592477B2

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