Potassium Persulfate → HCID 86736116, compound

HRID 971976Notes

Reaction equation

HRID 971976 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:9](=[O:10])[C@H:8]([N:11]=[N+:12]=[N-:13])[C@@H:7]1[CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+].COC1C=C(OC)C=CC=1C=O>C(#N)C.O>[CH3:19][O:18][CH:15]([O:16][CH3:17])[CH2:14][C@H:7]1[C@@H:8]([N:11]=[N+:12]=[N-:13])[C:9](=[O:10])[NH:6]1

Participants

7

Reactant 4

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, Dibasic2×HCID 691752,4-DimethoxybenzaldehydeHCID 53824762HCID 53824762, compound

Product 1

HCID 86736116HCID 86736116, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1.15 g (3.28 mmole) of cis-1-(2,4-dimethoxybenzyl)-2-(2,2-dimethoxyethyl)-3-azido-4-azetidinone in 120 ml of degassed acetonitrile was added at 80°, a solution of 11.8 g (43.7 mmole) of potassium persulfate and 4.05 g (23.3 mmole) of potassium monohydrogenphosphate in 135 ml of degassed water in 6 portions over a 1 hour period. The pH of the mixture was adjusted to 6.5- 7.0 with potassium monohydrogenphosphate after each addition. After one hour, the mixture was cooled to room temperature, the acetonitrile removed in vacuum and the pH adjusted to 8.0. Extraction with ethyl acetate (4× 75 ml) afforded a mixture of product and 2,4-dimethoxybenzaldehyde which was chromatographed over silica gel with benzene-ethyl acetate to give 0.51 g (77%) of the title compound as a light yellow oil.

Workup

  1. additionafter each addition
  2. customthe acetonitrile removed in vacuum
  3. extractionExtraction with ethyl acetate (4× 75 ml)
  4. customafforded
  5. customwas chromatographed over silica gel with benzene-ethyl acetate

Sources & evidence

ORD record
ord-91889e1f89a14d589544459a961caaf8
Source dataset
uspto-grants-1979_07
Patent number
US04162250

Reaction notes

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