Potassium Carbonate → HCID 90289950, Verbindung

HRID 1471629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471629
Br[C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:30][C:31]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10](=[O:11])[C@@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:30]=[CH2:31])[CH:3]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 90289952HCID 90289952, Verbindung

Produkt 1

HCID 90289950HCID 90289950, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A suspension of (S)-tert-butyl 3-(3-bromophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (6.3 g, 13.6 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.3 g, 20.4 mmol), potassium carbonate (54 ml, 0.4 M) and tetrakis(triphenylphosphine)palladium(0) (0.79 g, 0.68 mmol) in 50 ml of DME, was heated at reflux overnight. The suspension was cooled and filtered through celite. The filtrate was washed with brine and filtered through celite. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (15-35% EtOAc/hexanes) to provide the desired product (5.47 g, 13.33 mmol), 94%. MS (m/z) 411 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe suspension was cooled
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with brine
  6. filtrationfiltered through celite
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe crude product was introduced to a silica gel loading column
  11. custompurified by column chromatography (15-35% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-94faa4faca6846b7ab3e7ee0efbfd074
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012441B2

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