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

Citric Acid → (S)-4,5-bis((isobutoxycarbonyl)amino)pentyl methanesulfonate

HRID 62555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 62555
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:15][C:16](=[O:22])[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][NH:7][C:8](=[O:14])[O:9][CH2:10][CH:11]([CH3:13])[CH3:12].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH3:30][S:31]([O:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:15][C:16]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:22])[CH2:6][NH:7][C:8]([O:9][CH2:10][CH:11]([CH3:12])[CH3:13])=[O:14])(=[O:33])=[O:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131737193HCID 131737193, Verbindung

Produkt 1

HCID 90027162(S)-4,5-bis((isobutoxycarbonyl)amino)pentyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A round bottom flask was charged with (S)-diisobutyl (5-hydroxypentane-1,2-diyl)dicarbamate (5.0 g, 15.7 mmol), CH2Cl2 (80 mL), and triethylamine (5.3 mL, 38 mmol), and cooled to −78° C. Methanesulfonyl chloride (2.3 mL, 30 mmol) was added dropwise with stirring and the cold bath was allowed to warm to 0° C. over the course of 5 h. Aqueous citric acid (20%, 140 mL) and CH2Cl2 (150 mL) were added and the phases were separated. The organic phase was washed with saturated NaHCO3 solution, and then dried on anhydrous Na2SO4. The solvent was removed by rotary evaporation and dried in oil pump vacuum. The product (S)-4,5-bis((isobutoxycarbonyl)amino)pentyl methanesulfonate was obtained as a yellowish white solid. The crude product was used without further purification in the next procedure.

Aufarbeitung

  1. temperatureto warm to 0° C. over the course of 5 h
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated NaHCO3 solution
  4. dry with materialdried on anhydrous Na2SO4
  5. customThe solvent was removed by rotary evaporation
  6. customdried in oil pump vacuum

Quellen und Nachweise

ORD-Eintrag
ord-87a66e7d222641ecb55e53174d3e22fc
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09446393B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion