Dimethylformamide → HCID 86734330, compound

HRID 2050384Notes

Reaction equation

HRID 2050384 reaction equation
[O:1]=[C:2]1[NH:5][C@@H:4]([CH2:6]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:3]1[NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[N-:29]=[N+:30]=[N-:31].[Na+].CN(C)C=O.C(OCC)(=O)C>C(Cl)Cl>[N:29]([CH2:6][C@H:4]1[C@@H:3]([NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:2](=[O:1])[NH:5]1)=[N+:30]=[N-:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86734329cis-4-Oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine

Product 1

HCID 86734330HCID 86734330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing 1.131 g (2.8 mmole) of cis-4-oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine, 0.961 g (14.8 mmole) of sodium azide and 25 ml of anhydrous N,N-dimethylformamide was heated under argon at 40° for 6 hours then at ambient temperature for 24 hours. The reaction mixture was poured into ethyl acetate and was washed with water. The combined aqueous washes were extracted once with ethyl acetate and the ethyl acetate fractions were combined and extracted with brine. After drying the ethyl acetate solution (MgSO4) and filtering, the solvent was removed in vacuo to afford a yellow semi-crystalline residue. This residue was slurried in methylene dichloride and chromatographed on 25 g of silica gel (70-230 mesh). The 1:1 ethyl acetate:methylene dichloride fractions afforded the title compound; tlc: ethyl acetate, silica gel GF, Rf=0.38; mp 142°-143° (dec) (ethyl acetate-hexane).

Workup

  1. temperaturewas heated under argon at 40° for 6 hours
  2. washwas washed with water
  3. extractionThe combined aqueous washes were extracted once with ethyl acetate
  4. extractionextracted with brine
  5. dry with materialAfter drying the ethyl acetate solution (MgSO4)
  6. filtrationfiltering
  7. customthe solvent was removed in vacuo
  8. customto afford a yellow semi-crystalline residue
  9. customchromatographed on 25 g of silica gel (70-230 mesh)

Sources & evidence

ORD record
ord-66b9d575e9214c049119088834dba16b
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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