Acetyl chloride → HCID 178471808, Verbindung

HRID 420774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420774
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)[CH3:3].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:22](=[O:24])[CH3:23])[CH2:11][CH2:12]1)[CH3:3]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178471807HCID 178471807, Verbindung

Produkt 1

HCID 178471808HCID 178471808, VerbindungAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (1.0 g, 4.51 mmol) (Example A, step 2) was dissolved in dichloromethane and triethylamine (1.89 ml, 13.5 mmol) was added. Acetyl chloride (0.35 ml, 4.96 mmol) was added drop wise and the reaction mixture stirred for 5 hours at room temperature. The reaction mixture was quenched with saturated NaHCO3-solution and extracted with dichloromethane. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product (804 mg, 78%) [MS: m/e=228.3/229.3 (M+H+)] was obtained as a white solid and used without any further purification for the next step.

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated NaHCO3-solution
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c71d3e37f532465d96b64caa05cb7fb5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097637B2

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