Potassium Carbonate → HCID 66685270, Verbindung

HRID 579162

Reaktionsgleichung

Reaktionsgleichung von HRID 579162
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[S:12][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:15]=1Br)=[O:10].[C:23]([O:27][C:28]([N:30]1[CH2:35][C:34](=[O:36])[NH:33][C@H:32]([CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].O1CCOCC1>CCOC(C)=O.[Cu]I>[C:23]([O:27][C:28]([N:30]1[CH2:35][C:34](=[O:36])[N:33]([C:15]2[CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:12][C:11]=2[C:9]([O:8][CH3:7])=[O:10])[C@H:32]([CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 20775762Methyl 3-bromo-5-phenyl-thiophene-2-carboxylateHCID 66683955HCID 66683955, Verbindung

Produkt 1

HCID 66685270HCID 66685270, VerbindungAusbeute 29,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A tube was charged with trans-cyclohexanediamine (162 mg, 1.42 mmol, 0.5 equiv), K2CO3 (783 mg, 5.67 mmol, 2.0 equiv), 3-bromo-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.01 g, 3.40 mmol, 1.2 equiv), CuI (270 mg, 1.42 mmol, 0.5 equiv), (R)-3-Cyclohexyl-5-oxo-piperazine-1-carboxylic acid tert-butyl ester (800 mg, 2.83 mmol, 1.0 equiv) and 1,4-dioxane (3.0 mL). The tube was then flushed with N2 and sealed. The reaction mixtures were heated at 110° C. for 72 hours after which it was diluted with EtOAc and filtered. The filtrate was washed with 1.0 N HCl aq. solution, brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography (EtOAc/heptane, 50%) to give product (R)-3-Cyclohexyl-4-(2-methoxycarbonyl-5-phenyl-thiophen-3-yl)-5-oxo-piperazine-1-carboxylic acid tert-butyl ester 415 mg.

Aufarbeitung

  1. customThe tube was then flushed with N2
  2. customsealed
  3. customThe reaction mixtures
  4. filtrationfiltered
  5. washThe filtrate was washed with 1.0 N HCl aq. solution, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (EtOAc/heptane, 50%)

Quellen und Nachweise

ORD-Eintrag
ord-957f1efe45d64f02bdc55d90d5c9c129
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040690B2

Verknüpfte Notizen

Wird geladen…