Potassium Persulfate → 3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

HRID 65437

Reaction equation

HRID 65437 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C@H:9]([S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])[C@@H:8]([CH2:17][OH:18])[C:7]1=[O:19].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+]>C(#N)C>[OH:18][CH2:17][C@@H:8]1[C@@H:9]([S:10]([C:13]([CH3:15])([CH3:14])[CH3:16])(=[O:12])=[O:11])[NH:6][C:7]1=[O:19]

Participants

5

Reactant 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, DibasicHCID 186047711-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.butylsulphonyl-2-azetidinone

Product 1

HCID 186047743-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 74 mg (0.2 mmol) of 1-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.butylsulphonyl-2-azetidinone (see Example 20), 486 mg (1.8 mmol) of potassium peroxydisulphate and 174 mg (1.0 mmol) of dipotassium hydrogen phosphate in 4 ml of acetonitrile is stirred for 2 hours at 65° under a reflux condenser, the resulting reaction mixture is freed from acetonitrile under reduced pressure and the aqueous residue is extracted with ethyl acetate. After drying of the organic phase over Na2SO4 and concentration by evaporation in vacuo, a residue is obtained from which the title compound is obtained in the form of colourless crystals by adding a little methylene chloride and ether.

Workup

  1. customthe resulting reaction mixture
  2. extractionthe aqueous residue is extracted with ethyl acetate
  3. dry with materialAfter drying of the organic phase over Na2SO4 and concentration by evaporation in vacuo

Sources & evidence

ORD record
ord-aa853de2f5c04505a7cd89b5973f20c2
Source dataset
uspto-grants-1986_09
Patent number
US04614614

Linked notes

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