Sodium Azide → HCID 21426466, compound

HRID 258769Notes

Reaction equation

HRID 258769 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(O[CH2:9][C:10]1[CH2:17][S:16][CH:15]2[N:12]([C:13](=[O:28])[CH:14]2[NH:18][C:19](=[O:27])[CH2:20][C:21]2[S:22][C:23](=[O:26])[S:24][CH:25]=2)[C:11]=1[C:29]([OH:31])=[O:30])(=O)C>O.C(=O)(O)[O-].[Na+]>[N:1]([CH2:9][C:10]1[CH2:17][S:16][CH:15]2[N:12]([C:13](=[O:28])[CH:14]2[NH:18][C:19](=[O:27])[CH2:20][C:21]2[S:22][C:23](=[O:26])[S:24][CH:25]=2)[C:11]=1[C:29]([OH:31])=[O:30])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 21426457HCID 21426457, compound

Product 1

HCID 21426466HCID 21426466, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium azide (0.871 g.) is added to a solution of 3-acetoxymethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) in water (60 cc.) and sodium bicarbonate (0.588 g.), and the mixture is heated to 50° C. for 16 hours. It is allowed to cool and sodium bicarbonate (0.4 g.) is added. The mixture is extracted twice with ethyl acetate (40 cc.). The aqueous phase is treated with decolourising charcoal and brought to pH 2 by adding 6 N hydrochloric acid. A product precipitates, and is extracted with ethyl acetate (240 cc.). The organic extracts are dried over sodium sulphate and then concentrated to dryness under reduced pressure (20 mm.Hg). A residue (1.9 g.) is obtained, which is recrystallised from acetonitrile (18 cc.) to give 3-azidomethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (1.29 g.), m.p. 160° C., after a further recrystallisation from acetonitrile.

Workup

  1. temperatureto cool
  2. extractionThe mixture is extracted twice with ethyl acetate (40 cc.)
  3. additionThe aqueous phase is treated with decolourising charcoal
  4. additionby adding 6 N hydrochloric acid
  5. customA product precipitates
  6. extractionis extracted with ethyl acetate (240 cc.)
  7. dry with materialThe organic extracts are dried over sodium sulphate
  8. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  9. customA residue (1.9 g.) is obtained
  10. customwhich is recrystallised from acetonitrile (18 cc.)

Sources & evidence

ORD record
ord-922ddca637b64462800e95382e7a0304
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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