m-Chloroperbenzoic acid → HCID 59267897, compound

HRID 1809388Notes

Reaction equation

HRID 1809388 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>C(Cl)Cl>[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, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.62 g (21 mmol) of 2-(azetidine-1-sulfinyl)-2-methyl-propionic acid ethyl ester in DCM (100 mL) at room temperature are added 5.46 g (32 mmol) of meta-chloroperbenzoic acid. 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. The residue is dissolved in DCM (50 mL) and washed with a saturated aqueous NaHCO3 solution (50 mL). The organic layer is dried (Na2SO4) and filtered. The solvent is removed under reduced pressure to provide 5 g of 2-(azetidine-1-sulfonyl)-2-methyl-propionic acid ethyl ester as an orange oil, which is used in the next step without further purification. Yield 100%, ES-MS: m/z 236 [M+H].

Workup

  1. additionis introduced
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in DCM (50 mL)
  5. washwashed with a saturated aqueous NaHCO3 solution (50 mL)
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9865885724f54d17b362a5710c02ade1
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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