Ethyl Acetate → 4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide

HRID 7082

Reaktionsgleichung

Reaktionsgleichung von HRID 7082
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:29][CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH:32]=[CH:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[CH3:40]C1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(OCC)(=O)C>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24](/[CH:32]=[CH:33]/[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=3)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:29][CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 12500beta-MethylstyreneHCID 80271Tri-o-tolylphosphineHCID 220196094-[2-(tert-butoxycarbonylamino)ethoxy]-N-(3-iodophenyl)-3-methoxyphenylacetamide

Produkt 1

HCID 220195834-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamideAusbeute 152,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
97 °C

Versuchsvorschrift

Intermediate 4 (1 g) is dissolved in dimethylformamide (10 ml), and thereto are added 3-methylvinylbenzene (826 mg), palladium (II) acetate (105 mg), tris(2-methylphenyl)phosphine (143 mg), tetra-n-butyl ammonium chloride (130 mg), and the mixture is heated with stirring at 97° C. for 18 hours under argon atmosphere. To the reaction solution is added ethyl acetate, and the mixture is washed with water and 2 M hydrochloric acid. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-[2-(tert-butoxycarbonylamino)-ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (370 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (120 mg).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. washthe mixture is washed with water and 2 M hydrochloric acid
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-75cc4b5bd19f4a4696cb5248dd41f0c1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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