Triethylamine → 6-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-hex-5-ynoic acid

HRID 1253767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253767
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11](=[O:26])[NH:12][C:13]1[C:14]([CH3:25])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)[CH3:9].[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][CH2:30][C:31]#[CH:32].C(N(CC)CC)C>COCCOC.[Cu](I)I.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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:12][C:13]1[C:14]([CH3:25])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:32]#[C:31][CH2:30][CH2:29][CH2:28][C:27]([OH:34])=[O:33])=[CH:20][CH:19]=1)=[O:26])[CH3:9]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 1430365-Hexynoic acidHCID 67350786[5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

Produkt 1

HCID 462397756-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-hex-5-ynoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-chloro-phenyl)-ethyl ester (0.200 g, 0.46 mmol) and 5-hexynoic acid (0.06 mL, 0.55 mmol) in DME (5 mL) was added copper iodide (0.017 g, 0.09 mmol), followed by tetrakis(triphenylphosphine)palladium(0) (0.032 g, 0.05 mmol), and the mixture was purged with N2 for 5 minutes. Triethylamine (0.26 mL, 1.83 mmol) was added, and the reaction was purged with N2 for another 10 minutes and then stirred at 80° C. for 2 hours. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Aufarbeitung

  1. customthe mixture was purged with N2 for 5 minutes
  2. customthe reaction was purged with N2 for another 10 minutes
  3. customThe mixture was partitioned between EtOAc and H2O
  4. customthe aqueous layer was separated
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4981afb6c20e41f48f58fc85d928df87
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455499B2

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