Hydrochloric Acid → HCID 15023452, Verbindung

HRID 1613276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613276
[Cl:1][C:2]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].Cl.[NH2:19][CH2:20][C:21]#[C:22][CH2:23][OH:24].C(N(CC)CC)C.Cl>C(Cl)Cl>[OH:24][CH2:23][C:22]#[C:21][CH2:20][NH:19][C:3](=[O:4])[C:2]([Cl:1])([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 197755142-Chloro-2-cyclohexyl-2-phenylacetyl chlorideHCID 197755314-Aminobut-2-yn-1-ol hydrochloride

Produkt 1

HCID 15023452HCID 15023452, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-chloro-2-cyclohexyl-2-phenylacetyl chloride (9.0 g) in methylene chloride (50 ml) was added dropwise to a solution of 4-amino-2-butyn-1-ol hydrochloride (5.38 g) and triethylamine (30.8 ml) in methylene chloride (120 ml) at 0° C. The mixture was stirred at the same temperature for 10 minutes and then at room temperature for an additional 3.5 hours and 1N hydrochloric acid was added thereto. The organic layer was separated, washed with saturated sodium bicarbonate, aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (6:1) as an eluent to give N-(4-hydroxy-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide (7.32 g).

Aufarbeitung

  1. waitat room temperature for an additional 3.5 hours
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate, aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (6:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-e2e35deef8bb4e109acffb33141126f7
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05192779

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