Sodium Azide → HCID 23329746, compound

HRID 225321Notes

Reaction equation

HRID 225321 reaction equation
[NH2:1][CH:2]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26]Cl)[CH:20]=1)[C:3]([NH:5][CH:6]1[C:13](=[O:14])[N:12]2[CH:7]1[S:8][CH2:9][C:10]([CH3:18])=[C:11]2[C:15]([OH:17])=[O:16])=[O:4].[N-:28]=[N+:29]=[N-:30].[Na+]>O1CCCC1>[NH2:1][CH:2]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][N:28]=[N+:29]=[N-:30])[CH:20]=1)[C:3]([NH:5][CH:6]1[C:13](=[O:14])[N:12]2[CH:7]1[S:8][CH2:9][C:10]([CH3:18])=[C:11]2[C:15]([OH:17])=[O:16])=[O:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23329798HCID 23329798, compound

Product 1

HCID 23329746HCID 23329746, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-[[Amino[3-(chloromethyl)-4-hydroxyphenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (0.02 mole) is added to tetrahydrofuran at about 40° C. Sodium azide (0.04 mole) in tetrahydrofuran is added and the resulting mixture is stirred for 3 hours. The tetrahydrofuran is evaporated and the residue is treated with water to remove the sodium chloride and the excess sodium azide. The resulting residue is taken up in ethyl acetate and the ethyl acetate is dried over magnesium sulfate. Filtration removes the magnesium sulfate and removal of the ethyl acetate gives the title compound.

Workup

  1. customThe tetrahydrofuran is evaporated
  2. additionthe residue is treated with water
  3. customto remove the sodium chloride
  4. dry with materialthe ethyl acetate is dried over magnesium sulfate
  5. filtrationFiltration
  6. customremoves
  7. customthe magnesium sulfate and removal of the ethyl acetate

Sources & evidence

ORD record
ord-dbfa4b1c8abf4b0996eeec25f3e522ca
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Reaction notes

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