Potassium Carbonate → HCID 67682555, Verbindung

HRID 1751650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751650
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C@H:6]([C:19]2[NH:20][C:21]([C:24]3[CH:29]=[CH:28][C:27](B4OC(C)(C)C(C)(C)O4)=[CH:26][CH:25]=3)=[CH:22][N:23]=2)[CH2:5]1.Br[C:40]1[CH:45]=[CH:44][C:43]([C:46](=[O:56])[CH2:47][NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:42][CH:41]=1.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>[C:51]([O:50][C:49]([NH:48][CH2:47][C:46]([C:43]1[CH:42]=[CH:41][C:40]([C:27]2[CH:28]=[CH:29][C:24]([C:21]3[NH:20][C:19]([C@@H:6]4[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][N:7]4[C:9]([O:11][CH2:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[O:10])=[N:23][CH:22]=3)=[CH:25][CH:26]=2)=[CH:45][CH:44]=1)=[O:56])=[O:55])([CH3:54])([CH3:52])[CH3:53]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 59610197tert-butyl N-[2-(4-bromophenyl)-2-oxoethyl]carbamateHCID 67682938HCID 67682938, Verbindung

Produkt 1

HCID 67682555HCID 67682555, VerbindungAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

(2S,4S)-benzyl 4-(methoxymethyl)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (500 mg, 0.97 mmol), tert-butyl 2-(4-bromophenyl)-2-oxoethylcarbamate (364 mg, 1.16 mmol), Pd(PPh3)4 (112 mg, 0.097 mmol), and K2CO3 (2M in H2O, 1.6 mL, 3.2 mmoL) were combined in DME (10 mL). The mixture was degassed with bubbling N2 for 10 min the heated to 85° C. for 18 h. After cooling, the reaction mixture was diluted with EtOAc, and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc) to afford product (357 mg, 56%).

Aufarbeitung

  1. customThe mixture was degassed with bubbling N2 for 10 min the
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed successively with saturated aqueous NaHCO3 and brine
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b9c50ccc9dbc4772bbd576bb84a6b8f5
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156823B2

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