Trifluoroacetic acid → HCID 178449064, Verbindung

HRID 528996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528996
[CH2:1]([N:5]([CH2:43][CH2:44][CH2:45][CH3:46])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[N:11](COCC[Si](C)(C)C)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:43]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[NH:11][CH:12]=1)=[O:7])[CH2:44][CH2:45][CH3:46]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71062252Methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Produkt 1

HCID 178449064HCID 178449064, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (180 mg, 0.28 mmol) in DCM (4 mL) was added trifluoroacetic acid (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 4 h. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in DCM and washed with sat. NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated to give crude product. The crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3) to provide the title compound (130 mg, 91%). 1H NMR (CD3OD) δ 8.25-8.06 (m, 2H), 8.00-7.50 (m, 2H), 7.28-6.83 (m, 4H), 4.36 (br s, 1H), 4.01 (br s, 4H), 3.60-3.24 (m, 6H), 2.88-2.69 (m, 2H), 1.60-1.52 (m, 4H), 1.36-1.30 (m, 4H), 1.05-0.90 (m, 6H); MS(ESI−) m/z 515.2 (M−H)−.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in DCM
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-e2460e09de5942c790bc1da60c1f4e89
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

Notizen zur Reaktion

Wird geladen…