Triethylamine → HCID 66735700, Verbindung

HRID 1528613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528613
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][CH2:23][CH2:24][C:25]([CH2:31][CH:32]2[CH2:34][CH2:33]2)([OH:30])[CH2:26][C:27]([CH3:29])=[CH2:28])[CH3:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C@@H:20]([N:22]2[CH2:23][CH2:24][C:25]([CH2:31][CH:32]3[CH2:34][CH2:33]3)([CH2:26][C:27]([CH3:29])=[CH2:28])[O:30][C:2]2=[O:4])[CH3:21])=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67997442HCID 67997442, Verbindung

Produkt 1

HCID 66735700HCID 66735700, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphosgene (653 mg) was added to a solution of 1-[(S)-1-(4-bromophenyl)ethylamino]-3-(cyclopropylmethyl)-5-methylhex-5-en-3-ol (800 mg) and triethylamine (667 mg) in CH2Cl2 (15 mL) at 0° C. The mixture was stirred at room temperature overnight and the reaction was then quenched with water. The resulting mixture was extracted with CH2Cl2 and the combined organic layer was washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 3:1) to afford the title compound. Yield 670 mg (78% of theory).

Aufarbeitung

  1. customthe reaction was then quenched with water
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-b81737f02b4742c6bd7a7998c33245b4
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090605B2

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