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Hydrochloric Acid → 2-(4'-Methoxy-biphenyl-4-sulfonylamino)-3-methyl-butyric Acid Tert-butyl Ester

HRID 1292247
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1292247
[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 54389295HCID 54389295, Verbindung

Produkt 1

HCID 702120142-(4'-Methoxy-biphenyl-4-sulfonylamino)-3-methyl-butyric Acid Tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the 4-bromobenzenesulfonamide derivative (1 g, 2.64 mmol) prepared in Step (a) and 4-methoxybenzeneboronic acid (0.48 g, 3.17 mmol) in toluene (10 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.1 mmol) and aqueous sodium carbonate (0.5 g/5 mL H2O), respectively. The reaction mixture was refluxed for 3 hours, then cooled to room temperature. Ethyl acetate (25 mL) and aqueous HCl (1M, 25 mL) were added, the layers separated, and the organic portion was dried (MgSO4), filtered, and the filtrate was concentrated in vacuo. The resulting solid was triturated with hexane/ethyl acetate (3:1) and was collected by filtration. Yield: 0.68 g (62%);

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customthe layers separated
  3. dry with materialthe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting solid was triturated with hexane/ethyl acetate (3:1)
  7. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fd540a544afe4430a7a3fb1ef779d0da
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05756545

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