Tetrahydrofuran → HCID 20243624, compound

HRID 1659518Notes

Reaction equation

HRID 1659518 reaction equation
[CH:1]([CH:3]1[N:6]([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])[C:5](=[O:18])[CH:4]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:2].[O:30]1CCCC1>[Ag]=O.O>[C:1]([CH:3]1[N:6]([CH:7]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]([O:10][CH3:11])=[O:9])[C:5](=[O:18])[CH:4]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])([OH:30])=[O:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 20243610HCID 20243610, compound

Product 1

HCID 20243624HCID 20243624, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(4-formyl-2-oxo-3-phthalimido-1-azetidinyl)-2-phenylacetate (0.38 g.), silver oxide(0.92 g), tetra-hydrofuran (9 ml.) and water (1 ml.) was stirred at ambient temperature for 40 hours. The insoluble materials were filtered off from the reaction mixture and the tetrahydrofuran was removed by distillation from the filtrate under reduced pressure. Water was added to the resultant residue and adjusted to pH 2 with 10% hydrochloric acid, whereafter the mixture was extracted with ethyl acetate. The extract was washed with 1% Aqueous sodium bicarbonate, and the washings were adjusted to pH 2 with 10% hydrochloric acid. The aqueous solution was extracted with ethyl acetate, whereafter this extract and the above-obtained extract were combined, washed with water and then dried over magnesium sulfate. The solvent was removed by distillation from the solution under reduced pressure to give methyl 2-(4-carboxy-2-oxo-3-phthalimido-1-azetidinyl)-2-phenylacetate [a mixture of two cis isomers (a) and (b) at the third and fourth positions of the azetidine ring, (200 mg.)].

Workup

  1. filtrationThe insoluble materials were filtered off from the reaction mixture
  2. customthe tetrahydrofuran was removed by distillation from the filtrate under reduced pressure
  3. additionWater was added to the resultant residue
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with 1% Aqueous sodium bicarbonate
  6. extractionThe aqueous solution was extracted with ethyl acetate
  7. extractionwhereafter this extract
  8. extractionthe above-obtained extract
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was removed by distillation from the solution under reduced pressure

Sources & evidence

ORD record
ord-3fe83f3531bd4c51b00a24affbfcfb79
Source dataset
uspto-grants-1981_12
Patent number
US04304718

Reaction notes

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