Sodium Carbonate → 2-[2-tert-Butoxycarbonylamino-3-(4-phenyl-cyclohexa-1,5-dienyloxy)-propionylamino]-3-methylbutyric acid methyl ester

HRID 910423

Reaktionsgleichung

Reaktionsgleichung von HRID 910423
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][O:8][C:9](=[O:35])[CH:10]([NH:14][C:15](=[O:34])[CH:16]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)[CH:11]([CH3:13])[CH3:12].[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:7][O:8][C:9](=[O:35])[CH:10]([NH:14][C:15](=[O:34])[CH:16]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:21][CH:20]=1)[CH:11]([CH3:13])[CH3:12]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 666609032-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

Produkt 1

HCID 666609142-[2-tert-Butoxycarbonylamino-3-(4-phenyl-cyclohexa-1,5-dienyloxy)-propionylamino]-3-methylbutyric acid methyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2 M Na2CO3 (4 mL) was added at room temperature under an atmosphere of Argon to a mixture of the compound obtained in Example 22, step f (401 mg, 0.848 mmol), Pd(PPh3)2Cl2 (154 mg, 0.22 mmol) and phenylboronic acid (145 mg, 1.1872 mmol) in toluene (10 mL) and the reaction was heated to reflux. After 5 h, the reaction was cooled to room temperature. The mixture was diluted with EtOAc, and washed with brine. The combined organic layers were dried over anhydrous NaSO4 and concentrated under vacuum. The residue was purified by silica gel column chromatography which gave the title compound as a white solid (255 mg, 64%).

Aufarbeitung

  1. temperaturethe reaction was heated to reflux
  2. washwashed with brine
  3. dry with materialThe combined organic layers were dried over anhydrous NaSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography which

Quellen und Nachweise

ORD-Eintrag
ord-3a8fe606011848aeafd0d223340e9377
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022092B2

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