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

Triethylamine → HCID 12813314, Verbindung

HRID 2413185
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2413185
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[SH:29][CH2:30][C@@H:31]([CH3:42])[C:32]([N:34]1[C@H:38]([C:39]([OH:41])=[O:40])[CH2:37][S:36][CH2:35]1)=[O:33]>O1CCCC1.O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([S:29][CH2:30][C@@H:31]([CH3:42])[C:32]([N:34]2[C@H:38]([C:39]([OH:41])=[O:40])[CH2:37][S:36][CH2:35]2)=[O:33])=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 19266p-Acetamidobenzoic acidHCID 62365Isobutyl chloroformateHCID 171857YS 980

Produkt 1

HCID 12813314HCID 12813314, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

1.8 g of 4-acetylaminobenzoic acid is dissolved in 20 ml of dry tetrahydrofuran. To this solution, 1.4 ml of triethylamine is added. To this mixture, 1.3 ml of isobutyl chloroformate is added dropwise with stirring at -5° C. After ten minutes, to this solution, 20 ml of aqueous solution of 2.4 g of (4R)-3-[(2S)-3-mercapto-2-methylpropanoyl]-4-thiazolidinecarboxylic acid and 1.4 ml of triethylamine is added, and the mixture is stirred at room temperature for 30 min. To this reaction solution, 40 ml of water is added, and the obtained mixture is washed with ethyl acetate. The aqueous layer is acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give oil, yield 4.1 g. The oil is purified by silica gel column chromatography to give the titled compound, yield 3.6 g (90%), mp. 206°-207° C. (methanol), [α]D27 -152.5° (c=1.0, methanol).

Aufarbeitung

  1. waitAfter ten minutes
  2. stirringthe mixture is stirred at room temperature for 30 min
  3. washthe obtained mixture is washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give oil, yield 4.1 g
  9. customThe oil is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a618efcb44ac4645a880938411848cf2
Quelldatensatz
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04496578

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion