Tosylmethyl isocyanide → 3-Chloro-8-methyl-2-(5-oxazolyl)-8-azabicyclo[3.2.1]oct-2-ene oxalate

HRID 257449

Reaction equation

HRID 257449 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH2:14][CH:13]2[N:15]([CH3:16])[CH:10]([CH2:11][CH2:12]2)[C:9]=1[CH:17]=[O:18].S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH2:14][CH:13]2[N:15]([CH3:16])[CH:10]([CH2:11][CH2:12]2)[C:9]=1[C:17]1[O:18][CH:31]=[N:30][CH:29]=1

Participants

4

Reactant 2

HCID 161915Tosylmethyl isocyanideHCID 189608383-Chloro-2-formyl-8-methyl-8-azabicyclo[3.2.1]oct-2-ene oxalate

Product 1

HCID 189609363-Chloro-8-methyl-2-(5-oxazolyl)-8-azabicyclo[3.2.1]oct-2-ene oxalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-2-formyl-8-methyl-8-azabicyclo[3.2.1]oct-2-ene oxalate (0.55 g, 2 mmol) in 20 ml methanol powdered potassium carbonate (1.5 g) and tosylmethylisocyanide (0.4 g, 2 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. Upon evaporation in vacuo water (30 ml) was added to the residue and the water solution extracted with methylenechloride (3×20 ml). The combined methylenechloride extracts were dried and evaporated in vacuo. The residue was dissolved in ethanol, and the title compound precipitated with a 1M oxalic acid ether solution. The compound was filtered and dried. M.p. 69°-71° C. decomposes.

Workup

  1. customUpon evaporation in vacuo water (30 ml)
  2. additionwas added to the residue
  3. extractionthe water solution extracted with methylenechloride (3×20 ml)
  4. dry with materialThe combined methylenechloride extracts were dried
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethanol
  7. customthe title compound precipitated with a 1M oxalic acid ether solution
  8. filtrationThe compound was filtered
  9. customdried

Sources & evidence

ORD record
ord-d473129610c64b31b9e9b78f757962a4
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Linked notes

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