StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Chloroform → N-lauroyl-L-valine cyclohexylamide

HRID 1671747
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1671747
[C:1]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.ON1C(=O)CCC1=O.C(Cl)(Cl)Cl.[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C.C(N(CC)CC)C>[CH:35]1([NH:41][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 7965CyclohexylamineHCID 26658N-(1-Oxododecyl)-L-valineHCID 18987794N-Hydroxysuccinimide hydrate

Produkt 1

HCID 11523764N-lauroyl-L-valine cyclohexylamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471
Triethylamine
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

61 mg (0.20 mmol) of N-lauroyl-L-valine and 39 mg (0.26 mmol) of N-hydroxysuccinimide monohydrate were dissolved into 3.0 mL of dried chloroform. 50 mg (0.26 mmol) of 1-ethyl-3-(3-dimethylpropyl)carbodiimide hydrochloride was added thereto under argon atmosphere and in the ice bath, and stirred at 0° C. for 3 hours. 35 μL of triethylamine and 35 μL of cyclohexylamine were added thereto and stirred at room temperature overnight. Then, 20 mL of ethyl acetate was added thereto and washed with 25 mL of 0.2N hydrochloric acid, 20 mL of water and 20 mL of a saturated aqueous solution of sodium hydrogen carbonate. The mixture was then dried with anhydrous sodium sulfate and condensed under reduced pressure. The residue was purified with a thin-layer chromatography (silica gel, chloroform:methanol=20:1) to obtain 34 mg of N-lauroyl-L-valine cyclohexylamide (0.089 mmol, yield 44%).

Aufarbeitung

  1. washwashed with 25 mL of 0.2N hydrochloric acid, 20 mL of water and 20 mL of a saturated aqueous solution of sodium hydrogen carbonate
  2. dry with materialThe mixture was then dried with anhydrous sodium sulfate and condensed under reduced pressure
  3. customThe residue was purified with a thin-layer chromatography (silica gel, chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-9354f11cead54404a1a6b46abc7bb267
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07994353B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion