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

Hydrochloric Acid → (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 568265
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([O:23][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([OH:23])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20639577HCID 20639577, Verbindung

Produkt 1

HCID 70220671(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidineAusbeute 113,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342Acetonitrile
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (0.34 ml) is added dropwise to a solution of 372 mg of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer B), described in Synthesis Example 4-a), in 8.5 ml of dry acetonitrile under ice cooling (internal temperature 3° C.). The mixture is stirred in this state for 20 min and diluted with 50 ml of ethyl acetate, and the diluted solution is adjusted to pH 9.2 by addition of a 5% aqueous sodium hydrogencarbonate solution, followed by shaking. The organic layer is separated. The aqueous layer is extracted twice with 50 ml of ethyl acetate while adjusting the pH value to 9.2 by addition of a 5% aqueous sodium hydrogencarbonate solution. The organic layer is combined with the above organic layer, and the combined organic layers are dried over magnesium sulfate, followed by filtration and the removal of the solvent by evaporation under reduced pressure to give 313 mg of crude (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer B) as a slight yellow viscous material.

Aufarbeitung

  1. stirringby shaking
  2. customThe organic layer is separated
  3. extractionThe aqueous layer is extracted twice with 50 ml of ethyl acetate
  4. additionby addition of a 5% aqueous sodium hydrogencarbonate solution
  5. dry with materialthe combined organic layers are dried over magnesium sulfate
  6. filtrationfollowed by filtration
  7. customthe removal of the solvent
  8. customby evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd9afb23ef1e49e7a3a407b1f047bc06
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06180622B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion