Ethyl Acetate → 4-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate

HRID 2375236

Reaktionsgleichung

Reaktionsgleichung von HRID 2375236
[CH2:1]([O:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:33]([O:17][C:14]3[CH:13]=[CH:12][C:11]([C:10]([NH:9][O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:18])=[CH:16][CH:15]=3)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 27596461-(4-Methoxyphenyl)cyclohexanecarbonyl chlorideHCID 58611844N-(Benzyloxy)-4-hydroxybenzamide

Produkt 1

HCID 586118514-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N-(benzyloxy)4-hydroxybenzamide (14) (0.078 g, 0.32 mmol) and 4-dimethylaminopyridine (0.047 g, 0.38 mmol) in tetrahydrofuran (2 ml) under argon atmosphere at ice bath temperature a solution of 1-(4-methoxyphenyl) cyclohexanecarbonyl chloride (21a) (0.082 g, obtained in the preceding step of the synthesis) in tetrahydrofuran (2 ml) was added. The resultant white suspension was stirred at room temperature overnight and poured into ethyl acetate (80 ml). The ethyl acetate extract was washed with water (50 ml), brine (30 ml), and dried (Na2SO4). The solvent was evaporated and the residue was dissolved in a small amount of benzene (0.5-1 ml). The precipitated solid was filtered off, the filtrate was evaporated and chromatographed on silicagel (10 g) with benzene-ethyl acetate (9:1) as eluent affording the title compound (0.077 g, 52% based on 1/1) as a white solid. 1H NMR (DMSO-d6, HMDSO) δ: 1.07-2.01 (8H, m); 2.21-2.61 (2H, m, overlapped with a signal of DMSO); 3.75 (3H, s); 4.92 (2H, s); 6.97 (2H, d, J=8.5 Hz); 7.04 (2H, d, J=8.2 Hz); 7.23-7.54 (7H, m); 7.76 (2H, d, J=8.5 Hz); 11.77 (1H, s).

Aufarbeitung

  1. additionwas added
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (50 ml), brine (30 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in a small amount of benzene (0.5-1 ml)
  7. filtrationThe precipitated solid was filtered off
  8. customthe filtrate was evaporated
  9. customchromatographed on silicagel (10 g) with benzene-ethyl acetate (9:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-14aae1f8dfb841ce930c6398aee0f0e2
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465719B2

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