1,1'-(Diazomethylene)bis(benzene) → HCID 86739943, compound

HRID 615860Notes

Reaction equation

HRID 615860 reaction equation
[N:1]([C@H:4]1[C@@H:7]([CH2:8][O:9][CH2:10][C:11]([OH:13])=[O:12])[NH:6][C:5]1=[O:14])=[N+:2]=[N-:3].[C:15]1([C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N+]=[N-])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[C:15]1([CH:21]([O:12][C:11](=[O:13])[CH2:10][O:9][CH2:8][C@H:7]2[NH:6][C:5](=[O:14])[C@H:4]2[N:1]=[N+:2]=[N-:3])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 86739942HCID 86739942, compound

Product 1

HCID 86739943HCID 86739943, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (±)-(cis)-[(3-azido-2-oxo-4-azetidinyl)methoxy]acetic acid (0.880 g, 4.42 mmole) was treated with a solution of diphenyl diazomethane (858 mg, 4.42 mmole) in acetone (12 ml). The reaction was stirred at room temperature for nineteen hours and then combined with another run (621 mg acid, 3.12 mmole). The solvent was removed in vacuo and ethyl acetate was added and evaporated. The residue was dissolved in ethyl acetate (70 ml), dried (sodium sulfate), filtered, and concentrated to 2.6 g of a heavy yellow-red oil. The crude product was chromatographed on silica gel (230-400 mesh, 100 g) with 50% hexane-ethyl acetate. Concentration of the appropriate fractions and removal of solvents produced a heavy oil which was triturated with ether to produce a white solid which was filtered and dried to yield 1.34 g of the title compound. An additional 463 mg was obtained from the mother liquor. The total yield was 1.804 g.

Workup

  1. customThe solvent was removed in vacuo and ethyl acetate
  2. additionwas added
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (70 ml)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to 2.6 g of a heavy yellow-red oil
  8. customThe crude product was chromatographed on silica gel (230-400 mesh, 100 g) with 50% hexane-ethyl acetate
  9. customConcentration of the appropriate fractions and removal of solvents
  10. customproduced a heavy oil which
  11. customwas triturated with ether
  12. customto produce a white solid which
  13. filtrationwas filtered
  14. customdried

Sources & evidence

ORD record
ord-aa2571fdce064e8a965a7904714d1f97
Source dataset
uspto-grants-1985_02
Patent number
US04501697

Reaction notes

Loading…