Sodium Azide → HCID 19602504, compound

HRID 1604250Notes

Reaction equation

HRID 1604250 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH:7]1[O:13][CH:12]2[N:9]([C:10](=[O:14])[CH2:11]2)[CH2:8]1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O.C(OCC)(=O)C>[N:15]([CH2:2][C:3]([NH:5][CH2:6][CH:7]1[O:13][CH:12]2[N:9]([C:10](=[O:14])[CH2:11]2)[CH2:8]1)=[O:4])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 19602469HCID 19602469, compound

Product 1

HCID 19602504HCID 19602504, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3RS,5RS)-3-(N-Chloroacetylaminomethyl)-4-oxa-1-azabicyclo[3.2.0]heptan-7-one(500 mg), of example 8, and Sodium azide(297 mg) were stirred in Dimethyl sulfoxide(10 ml) at room temperature for 14 hrs. The reaction mixture was diluted with Ethyl acetate, washed with water, brine and dried over Magnesium sulfate. The residue, which obtained after removal of solvent in vacuo, was purified by silicagel column chromatography (Hexane+Ethyl acetate 1:2). The title compound was obtained as oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Magnesium sulfate
  3. customThe residue, which obtained
  4. customafter removal of solvent in vacuo
  5. customwas purified by silicagel column chromatography (Hexane+Ethyl acetate 1:2)

Sources & evidence

ORD record
ord-fed6e40ea7fe48eead2768477c4e7a1d
Source dataset
uspto-grants-1999_11
Patent number
US05994342

Reaction notes

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