HCID 21185506, Verbindung → {4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester

HRID 254370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254370
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10](=[O:19])[NH:11][C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][C:33]#[CH:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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.[Cu](I)I.C(N(CC)CC)C>[CH2:21]([O:28][C:29](=[O:35])[NH:30][CH2:31][CH2:32][C:33]#[C:34][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10](=[O:19])[CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20])=[CH:13][CH:14]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 2

HCID 21185506HCID 21185506, VerbindungHCID 29404500[2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Produkt 1

HCID 58664814{4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of [2-(4-iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester 310 (1.5 g, 3.84 mmol), and triethylamine (40 mL) was added trans-dichlorobis-(triphenylphosphine)palladium (II) (Ph3P, PdCl2, 0.27 g, 0.38 mmol). The reaction mixture was stirred for 20 minutes when it became a clear solution. But-3-ynyl-carbamic acid benzyl ester (0.94 g, 4.6 mmol) and copper iodide (0.14 g, 0.768 mmol) were then added and the reaction was further stirred at room temperature for 18 hours. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (100 mL) and washed with water (3×150 mL). The organic layer was dried over sodium sulfate and then concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 1:1, v/v hexanes/ethyl acetate) to provide 320 (1.91 g, still a mixture, but used as it was without further purification). 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 2.60 (m, 4H), 3.47 (m, 4H), 5.12 (s, 2H), 7.37 (m, 7H), 7.49 (d, 2H).

Aufarbeitung

  1. stirringthe reaction was further stirred at room temperature for 18 hours
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. washwashed with water (3×150 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 1:1, v/v hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9795a5091ea94f40b4342a55f127d035
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875619B2

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