Hydrochloric Acid → HCID 20559124, compound

HRID 482846Notes

Reaction equation

HRID 482846 reaction equation
[N:1]([CH:4]1[CH:7]([CH:8]=[O:9])[N:6]([CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])[C:5]1=[O:21])=[N+:2]=[N-:3].[BH4-].[Na+].Cl.[Cl-].[Na+]>C(O)C.O>[N:1]([CH:4]1[CH:7]([CH2:8][OH:9])[N:6]([CH:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:11]([O:13][CH3:14])=[O:12])[C:5]1=[O:21])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 20243661HCID 20243661, compound

Product 1

HCID 20559124HCID 20559124, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of methyl 2-(3-azido-4-formyl-2-oxo-1-azetidinyl)-2-phenylacetate (2.30 g.), sodium borohydride (310 mg), ethanol (40 ml.) and water (5 ml.) was stirred at -10° to 0° C. for an hour. The reaction mixture was adjusted to pH 4 to 5 with 10% hydrochloric acid at the same temperature, whereafter the ethanol was removed by distillation from the solution to give an aqueous residue, to which sodium chloride was added. The resultant solution was extracted twice with chloroform and the extract was washed with an aqueous sodium chloride. After drying the solution over magnesium sulfate, the solution was evaporated to dryness under reduced pressure to give a residue(2.02 g.), which was subjected to column chromatography on alumina(20 g.). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solvent was removed by distillation under reduced pressure to give methyl 2-(3-azido-4-hydroxymethyl-2-oxo-1-azetidinyl)-2-phenylacetate(0.95 g.).

Workup

  1. customwas removed by distillation from the solution
  2. customto give an aqueous residue
  3. extractionThe resultant solution was extracted twice with chloroform
  4. washthe extract was washed with an aqueous sodium chloride
  5. dry with materialAfter drying the solution over magnesium sulfate
  6. customthe solution was evaporated to dryness under reduced pressure
  7. customto give a residue(2.02 g.), which
  8. washElution
  9. additionthe fractions containing a desired compound
  10. customwere collected
  11. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f7aa1facfd654a278fc05447ef67fc42
Source dataset
uspto-grants-1986_03
Patent number
US04576753

Reaction notes

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