Sodium Phosphate, Dibasic → 4-Carbomethoxy-3-phthalimido-azetidin-2-one

HRID 127904

Reaction equation

HRID 127904 reaction equation
[C:1]([CH:5]1[N:8](CC2C=CC(OC)=CC=2)[C:7](=[O:18])[CH:6]1[N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])([O:3][CH3:4])=[O:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P(O)([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[C:1]([CH:5]1[NH:8][C:7](=[O:18])[CH:6]1[N:19]1[C:20](=[O:29])[C:21]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:22]2[C:23]1=[O:24])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 24412Potassium PersulfateHCID 234701784-Carbomethoxy-3-phthalimido-1-(p-methoxybenzyl)azetidin-2-one

Product 1

HCID 234700614-Carbomethoxy-3-phthalimido-azetidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.45 g (6.22 mmol) of the azetidinone in 250 ml of acetonitrile and 75 ml of water was degassed with argon. At 80°, a degassed solution of 23.5 g (87.2 mmol) of potassium persulfate and 7.77 g (55 mmol) of disodium phosphate was added in 6 portions over 1 hour. The mixture was cooled, the acetonitrile removed in vacuum, the aqueous residue saturated with sodium chloride and extracted with warm (40°) hexane (3×100 ml) then with ethyl acetate (5×125 ml). The ethyl acetate extract was washed with sodium bicarbonate, brine, dried and evaporated to dryness. Titration with ether gave 4-carbomethoxy-3-phthalimido-azetidin-2-one, m.p. 124°-6°.

Workup

  1. temperatureThe mixture was cooled
  2. customthe acetonitrile removed in vacuum
  3. extractionthe aqueous residue saturated with sodium chloride and extracted
  4. temperaturewith warm (40°) hexane (3×100 ml)
  5. extractionThe ethyl acetate extract
  6. washwas washed with sodium bicarbonate, brine
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-af3051de722f49048d2c77dc82adbbf0
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Linked notes

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