Acetone → HCID 19602485, compound

HRID 1604251Notes

Reaction equation

HRID 1604251 reaction equation
[N:1]([CH2:4][C:5]([NH:7][CH2:8][CH:9]1[O:15][CH:14]2[N:11]([C:12](=[O:16])[CH2:13]2)[CH2:10]1)=[O:6])=[N+:2]=[N-:3].[CH3:17][C:18](C)=O>>[N:1]1([CH2:4][C:5]([NH:7][CH2:8][CH:9]2[O:15][CH:14]3[N:11]([C:12](=[O:16])[CH2:13]3)[CH2:10]2)=[O:6])[CH:18]=[CH:17][N:3]=[N:2]1

Participants

3

Reactant 2

HCID 180AcetoneHCID 19602504HCID 19602504, compound

Product 1

HCID 19602485HCID 19602485, compoundYield 69%

Conditions

Temperature
65 °C

Procedure

150 mg of (3RS,5RS)-3-[N-(Azidoacetyl)aminomethyl]-4-oxa-1-azabicyclo[3.2.0]heptan-7-one was dissolved in 10 ml of Acetone and Acetylene was bubbled at -78° C. for 5 minutes. The reaction mixture was heated at 60-70° C. in seal tube for 17 hrs. After reaction completed, solvent was removed in vacuo and the residue was purified by silicagel column chromatography (Ethyl acetate+Acetone 3:1). The title compound was obtained as oil.

Workup

  1. customAcetylene was bubbled at -78° C. for 5 minutes
  2. customAfter reaction
  3. customsolvent was removed in vacuo
  4. customthe residue was purified by silicagel column chromatography (Ethyl acetate+Acetone 3:1)

Sources & evidence

ORD record
ord-6c193b8c831e41efb04b40948c9c5840
Source dataset
uspto-grants-1999_11
Patent number
US05994342

Reaction notes

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