Potassium Carbonate → HCID 86590134, Verbindung

HRID 1840521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840521
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[CH:25])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I.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>[CH3:13][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[C:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:11]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

Produkt 1

HCID 86590134HCID 86590134, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-bromo-5-nitropyridine (10.0 g; 49.0 mmol), methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pent-4-ynoate (13.34 g; 58.8 mmol), copper iodide (0.465 g; 2.5 mmol), potassium carbonate (13.6 g; 98.0 mmol) and dichlorobis(triphenylphosphine)palladium (1.7 g; 2.5 mmol) in 30 ml of anhydrous dimethylformamide (DMF) is heated for 4 hours at 60° C. under argon. The reaction mixture is taken up in 800 ml of ethyl acetate, washed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine, dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a column of silica, eluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate. 11 g of methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(5-nitropyrid-2-yl)pent-4-ynoate is isolated.

Aufarbeitung

  1. washwashed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-faa9066029644151b344ebe3cf4afd74
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680329B2

Notizen zur Reaktion

Wird geladen…