Sodium Azide → 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 442359Notes

Reaction equation

HRID 442359 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:26])[CH:10]2[NH:14][C:15](=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=2)[C:7]=1[C:27]([OH:29])=[O:28])(=[O:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+]>CO>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:26])[CH:10]2[NH:14][C:15](=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:30]=[N+:31]=[N-:32])=[CH:19][CH:18]=2)[C:7]=1[C:27]([OH:29])=[O:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 233432303-[(Acetyloxy)-methyl]-7-[[2-[4-(chloromethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 227677583-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A warm solution of 1 g of 3-[(acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid and 2 g. of sodium azide in 80 ml of methanol was refluxed for 4 hours after which the solvent was removed under high vacuum at room temperature. The residue was triturated with 80 ml of benzeneacetone (2:1) to give 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2carboxylic acid. M.P. 135°-136° C.

Workup

  1. customwas removed under high vacuum at room temperature
  2. customThe residue was triturated with 80 ml of benzeneacetone (2:1)

Sources & evidence

ORD record
ord-b7ccf47cd68242679da678661e8dd498
Source dataset
uspto-grants-1977_08
Patent number
US04045438

Reaction notes

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