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Ammonium Chloride → Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

HRID 503910
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 503910
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]([O:10][C:11](=[O:26])[NH:12][CH2:13][CH:14]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[CH3:25])[CH2:15][CH2:16][OH:17])([CH3:9])([CH3:8])[CH3:7].[NH4+].[Cl-]>C(Cl)Cl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH:14]([CH2:13][NH:12][C:11]([O:10][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:26])[CH2:15][CH2:16][O:17][S:1]([CH3:4])(=[O:3])=[O:2])=[C:19]([CH3:25])[CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 66877268[2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 86621498Methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Mesyl chloride (7.53 mL, 0.09726 mol) was added, at −78° C., to a solution of [2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester (30.3 g, 0.08457 mol) in DCM (600 mL) followed by TEA (27 mL, 0.1945 mol). The reaction mixture was stirred at −78° C. for 1 hour, then allowed to reach room temperature with stirring for an additional hour. A saturated aqueous solution of NH4Cl was added, and the resulting mixture was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and evaporated under reduced pressure to give methanesulfonic acid 3-(4-bromo-2-methyl-phenyl)-4-tert-butoxycarbonylamino-butyl ester, which was used without further purification.

Aufarbeitung

  1. customto reach room temperature
  2. stirringwith stirring for an additional hour
  3. extractionthe resulting mixture was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-102b2e1bb456495982465ca71248e3b6
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776910B2

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