2,3,5,6-Tetrafluorophenol → tert-Butyl pentanoate

HRID 634935

Reaktionsgleichung

Reaktionsgleichung von HRID 634935
[F-].[K+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][CH:27]([C:36](=[O:39])[CH2:37]Br)[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18].[F:40][C:41]1[C:46]([F:47])=[CH:45][C:44]([F:48])=[C:43]([F:49])[C:42]=1[OH:50]>CN(C=O)C>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][CH:27]([C:36](=[O:39])[CH2:37][O:50][C:42]1[C:43]([F:49])=[C:44]([F:48])[CH:45]=[C:46]([F:47])[C:41]=1[F:40])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18].[C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])(=[O:30])[CH2:28][CH2:27][CH2:36][CH3:37]

Komponenten

6

Edukt 3

HCID 698582,3,5,6-TetrafluorophenolHCID 522689Potassium FluorideHCID 86756359N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester

Produkt 2

HCID 520048tert-Butyl pentanoateAusbeute 371,5 %HCID 86756358N-[(1-methyl-3-isobutyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium fluoride (21.6 mg, 0.37 mmol) was added to a solution of N-[(1-methyl-3-isobutyl-indole-2-carbonyl)valinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester (86.1 mg, 0.149 mmol) and 2,3,5, 6-tetrafluorophenol (27.0 mg, 0.163 mmol) in DMF (2.0 ml). After stirring at room temperature for 3 hours, the reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was back-extracted with ethyl acetate. The organic layers were combined, washed with saturated NaHCO3 solution, and brine, dried over sodium sulfate, and concentrated. The residue was triturated with ether to give the titled product, N-(1-methyl-3-isobutyl-indole-2-carbonyl)-valinyl-3-amino-4-oxo-5-(2,3,5,6-tetral]uorophenyloxy)-pentanoic acid, tert-butyl ester as a white solid (43.8 mg, 44%). TLC (hexane/EtOAc, 50/50): Rf=0.50.

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was back-extracted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution, and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-6da38b4177ff47fe80c51126986009bb
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184244B2

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