m-Chloroperbenzoic acid → HCID 59267897, compound

HRID 1037574Notes

Reaction equation

HRID 1037574 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]([S:8]([N:10]1[CH2:13][CH2:12][CH2:11]1)=[O:9])([CH3:7])[CH3:6])[CH3:2].ClC1C=CC=C(C(OO)=[O:23])C=1>ClCCl>[CH2:1]([O:3][C:4](=[O:14])[C:5]([S:8]([N:10]1[CH2:11][CH2:12][CH2:13]1)(=[O:23])=[O:9])([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59267857Ethyl 2-(1-azetidinylsulfinyl)-2-methylpropanoate

Product 1

HCID 59267897HCID 59267897, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(azetidine-1-sulfinyl)-2-methyl-propionic acid ethyl ester (4.62 g, 21 mmol) in dichloromethane (100 mL) at room temperature is added meta-chloroperbenzoic acid (5.46 g, 32 mmol). The reaction is stirred for 1 h before Ambersep 900-OH resin (2.9 g) is introduced. The suspension is shaken for 2 h and then filtered. The filtrate is concentrated under reduced pressure and the residue is re-dissolved in dichloromethane (50 mL), washed with a saturated solution of sodium bicarbonate (50 mL) and the solvent is concentrated under reduced pressure to provide the title compound as an orange oil. This oil is used without further purification, m/z 236 [M+H+].

Workup

  1. additionis introduced
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionthe residue is re-dissolved in dichloromethane (50 mL)
  5. washwashed with a saturated solution of sodium bicarbonate (50 mL)
  6. concentrationthe solvent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-3eb33c288c504aa79e41b0178cdda624
Source dataset
uspto-grants-2013_10
Patent number
US08546563B2

Reaction notes

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