Methanol → HCID 20243574, compound

HRID 1659514Notes

Reaction equation

HRID 1659514 reaction equation
[CH3:1]N(C)CCCN.CO.C(Cl)(Cl)Cl.[O:14]=[C:15]1[CH:18]([N:19]2C(=O)C3=CC=CC=C3C2=O)[CH2:17][N:16]1[CH:30]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)[C:31]([O-:33])=[O:32]>C(OCC)(=O)C>[NH2:19][CH:18]1[CH2:17][N:16]([CH:30]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)[C:31]([O:33][CH3:1])=[O:32])[C:15]1=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 20243657HCID 20243657, compound

Product 1

HCID 20243574HCID 20243574, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethyl-1,3-propanediamine (1.32 g.) was added to a mixture of methanol (30 ml.) and chloroform (18 ml.) containing 2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(2-thienyl)-acetate (2.22 g.), whereafter the mixture was stirred at ambient temperature overnight. After the reaction, the reaction mixture was evaporated to dryness under reduced pressure to give a residue, which was dissolved in ethyl acetate. The solution was extracted with three portions of an aqueous solution consisting of 1 N hydrochloric acid (6.4 ml.) and water (10 ml.). The combined aqueous extracts were adjusted to pH8 with sodium bicarbonate and then saturated with sodium chloride. The solution was extracted with ethyl acetate and the extract was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. The solution was evaporated to dryness under reduced pressure to give a residue (1.57 g.), which was subjected to column chromatography on silica gel (25 g.). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solvent was removed by distillation from the solution under reduced pressure to give methyl 2-(3-amino-2-oxo-1-azetidinyl)-2-(2-thienyl)acetate (0.96 g.).

Workup

  1. customAfter the reaction
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. customto give a residue, which
  4. extractionThe solution was extracted with three portions of an aqueous solution
  5. extractionThe solution was extracted with ethyl acetate
  6. washthe extract was washed with a saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe solution was evaporated to dryness under reduced pressure
  9. customto give a residue (1.57 g.), which
  10. washElution
  11. additionthe fractions containing a desired compound
  12. customwere collected
  13. customThe solvent was removed by distillation from the solution under reduced pressure

Sources & evidence

ORD record
ord-21c21917fa074059878c6e3d4f0afa9f
Source dataset
uspto-grants-1981_12
Patent number
US04304718

Reaction notes

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