Water → HCID 70619213, compound

HRID 2083187Notes

Reaction equation

HRID 2083187 reaction equation
C([N:14]1[C:17](=[O:18])[C@H:16]([N:19]2[C:23](=[O:24])[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[C@@H:15]1[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:31])(C1C=CC=CC=1)C1C=CC=CC=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].O.O.O.O.O.O.O.O.O.O.O.O.P(O)([O-])([O-])=O.[Na+].[Na+].O>C(#N)C>[C:20]1(=[O:29])[N:19]([C@H:16]2[C:17](=[O:18])[NH:14][C@H:15]2[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:31])[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

6

Reactant 4

HCID 962WaterHCID 24412Potassium PersulfateHCID 61456Phosphoric acid, disodium salt, dodecahydrateHCID 70619372HCID 70619372, compound

Product 1

HCID 70619213HCID 70619213, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 250 mg of butyl cis-1-benzhydryl-3-phthalimido-4-oxo-2-azetidine carboxylate, 473 mg (1.75 mmole) of potassium persulfate, 307 mg (0.858 mmole) of disodium phosphate dodecahydrate, 9.2 ml of water and 8.4 ml of acetonitrile is thoroughly degassed with argon and then heated to 80°-85° under argon for three hours. The reaction mixture is cooled and the acetonitrile removed on the rotary evaporator. The aqueous residue is saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic extractions are washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give crude butyl cis-3-phthalimido-4-oxo-2-azetidinecarboxylate.

Workup

  1. customis thoroughly degassed with argon
  2. temperatureheated to 80°-85° under argon for three hours
  3. temperatureThe reaction mixture is cooled
  4. customthe acetonitrile removed on the rotary evaporator
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined organic extractions
  7. washare washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1203e67aad46494ab544c4b66fca98c2
Source dataset
uspto-grants-1978_04
Patent number
US04085100

Reaction notes

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