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

Methanesulfonyl chloride → (S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate

HRID 1697258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1697258
[Si:1]([O:8][C@H:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)(C)(=O)=O.CC([O-])(C)C.[K+]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([CH:10]1[CH2:11][N@@:13]1[C:14]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:20])[CH2:21][O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 86635712tert-butyl (2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-hydroxybutan-2-ylcarbamate

Produkt 1

HCID 86635713(S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of tert-butyl (2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-hydroxybutan-2-ylcarbamate (1.025 g, 2.3 mmol) in 20 mL DCM was cooled to 0° C., treated with N,N-DIPEA (0.60 ml, 3.4 mmol) followed by Ms-Cl (0.18 ml, 2.3 mmol). After stirring at 0° C. for 2 hours, the reaction mixture was concentrated in vacuo and the crude residue was dissolved in 20 mL THF. KOt-Bu (0.51 g, 4.6 mmol) was added, and the reaction mixture was allowed to stir at RT for 10 minutes. The reaction mixture was then diluted with EtAOc, washed with water then brine. The organics dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave (S)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate as a clear oil.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionthe crude residue was dissolved in 20 mL THF
  3. stirringto stir at RT for 10 minutes
  4. additionThe reaction mixture was then diluted with EtAOc
  5. washwashed with water
  6. dry with materialThe organics dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4bd087b12c744616b39de9cada4ebf60
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163909B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion