Triethylamine → (E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester

HRID 220182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220182
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1.[C:21]([O:25][C:26](=[O:39])[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:38])[CH:36]=[CH2:37])([CH3:24])([CH3:23])[CH3:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](/[CH:37]=[CH:36]/[C:35](=[O:38])[NH:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:39])=[CH:15][CH:14]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195, VerbindungHCID 592382632-(4-Bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester

Produkt 1

HCID 59238287(E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-3-(1-methyl-piperidin-4-yl)-propionic acid methyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester (2.27 g, 6.67 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (2 g, 7.2 mmol), Pd2(dba)3 (160 mg, 0.175 mmol), tri-o-tolylphosphine (160 mg, 0.526 mmol) and triethylamine (1.6 g, 15.8 mmol) in DMF (12 mL) was stirred at 100 degrees Celsius under N2 for 4 hours. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NH4Cl, and extracted with ethyl acetate (80 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography to obtain a pale yellow solid (1.74 g, 50%). MS: calc'd 522 (MH+), exp 522 (MH+).

Aufarbeitung

  1. extractionextracted with ethyl acetate (80 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01faed2728e946bd9ab4e6be7a148f19
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202866B2

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