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

HRID 1819493Notes

Reaction equation

HRID 1819493 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a7f1f5a7fc954676a375da54cc698c83
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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