Sodium Sulfite → (2-Methanesulfonyl-benzyl)-carbamic acid tert-butyl ester

HRID 1819493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819493
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[C:12]([O:16][C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1SC)([CH3:15])([CH3:14])[CH3:13].[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+]>C(Cl)Cl>[C:12]([O:16][C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=1[S:29]([CH3:1])(=[O:32])=[O:30])([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 22464516N-Boc-2-(methylthio)-benzylamine

Produkt 1

HCID 22464527(2-Methanesulfonyl-benzyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

MCPBA (60%, 5.82 g, 20.2 mmol) was added to a solution of (2-methylsulfanyl-benzyl)-carbamic acid tert-butyl ester (2.5 g, 9.87 mmol) in DCM (100 mL) which was pre-cooled to 0 degrees C. After 5 h, 100 ml of a 10% aqueous solution of sodium sulfite (Na2SO3) was added to the reaction and the organic layers were collected, washed with saturated aqueous sodium carbonate (50 mL), dried over MgSO4, filtered and concentrated in-vacuo. Chromatography (silica, 0-15% MeOH in DCM) yielded 1.885 g of (2-methanesulfonyl-benzyl)-carbamic acid tert-butyl ester as an off-white solid.

Aufarbeitung

  1. customthe organic layers were collected
  2. washwashed with saturated aqueous sodium carbonate (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a7f1f5a7fc954676a375da54cc698c83
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601714B2

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