Sodium Azide → cis-4-Azidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine

HRID 978877Notes

Reaction equation

HRID 978877 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10]I)[C@H:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:22].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C)C=O>[N:29]([CH2:10][C@H:9]1[N:6]([CH2:5][C:4]2[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:3]=2[O:2][CH3:1])[C:7](=[O:22])[C@H:8]1[NH:12][C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 70391052HCID 70391052, compound

Product 1

HCID 86740464cis-4-Azidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6 ml of N,N-dimethylformamide are added 740 mg of cis-1-(2,4-dimethoxybenzyl)-4-iodomethyl-3-phenylacetamido-2-oxoazetidine and 146 mg of sodium azide and the mixture is stirred for 4 days at room temperature. The solvent is distilled off in vacuo, and ethyl acetate and water are added to the residue. The ethyl acetate layer is separated, washed with an aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off in vacuo. To the residue, ether is added and the precipitated crystals are collected by filtration to give cis-4-azidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine, m.p. 110°-111° C.

Workup

  1. distillationThe solvent is distilled off in vacuo, and ethyl acetate and water
  2. additionare added to the residue
  3. customThe ethyl acetate layer is separated
  4. washwashed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off in vacuo
  7. additionTo the residue, ether is added
  8. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-b2bbf2374bf041b28b89e2c76e3fc55a
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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