Hydrochloric Acid → HCID 21426469, compound

HRID 258776Notes

Reaction equation

HRID 258776 reaction equation
[Na].C(O[CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:25])[CH:11]2[NH:15][C:16](=[O:24])[CH2:17][C:18]2[S:19][C:20](=[O:23])[S:21][CH:22]=2)[C:8]=1[C:26]([OH:28])=[O:27])(=O)C.[S-]C#N.[K+].C(=O)(O)[O-].[Na+].[CH3:38][N:39]1[N:43]=[N:42][C:41](=[S:44])[NH:40]1.Cl.C(OC(C)C)(C)C>O.O1CCCC1>[C:26]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][S:44][C:41]1[N:42]=[N:43][N:39]([CH3:38])[N:40]=1)[CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]1[S:19][C:20](=[O:23])[S:21][CH:22]=1)[C:10]2=[O:25])([OH:28])=[O:27]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 199940532-Methyl-1,2-dihydro-5H-tetrazole-5-thioneHCID 21426457HCID 21426457, compound

Product 1

HCID 21426469HCID 21426469, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The sodium salt 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 (6.1 g.) is dissolved in water (20 cc.). Potassium thiocyanate (26.6 g.), sodium bicarbonate (1.38 g.) and 2-methyl-5-thioxo-1,2,3,4-tetrazoline (1.9 g.) are added to this solution and the mixture is heated to 60° C. for 5 hours. After cooling, the reaction mixture is diluted with water (100 cc.), acidified to pH 5.8 by adding 4 N hydrochloric acid and washed with ethyl acetate (50 cc.). The aqueous phase is acidified to pH 1.6 by adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.). After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (a total of 200 cc.). The organic extracts are combined, washed twice with an 0.1 N hydrochloric acid solution (a total of 140 cc.) and then twice with water (a total of 200 cc.), dried over sodium sulphate, treated with decolourising charcoal, filtered and then concentrated to dryness under reduced pressure (20 mm Hg). The residue obtained is dissolved in tetrahydrofuran (25 cc.) and this solution is then added dropwise to isopropyl ether (300 cc.). A product precipitates which is isolated by filtration and dried under reduced pressure (0.1 mm Hg). 2-Carboxy-3[(2-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (5.1 g.) is thus obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with ethyl acetate (50 cc.)
  3. additionby adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.)
  4. customAfter decanting the organic phase
  5. extractionthe aqueous phase is extracted twice with ethyl acetate (a total of 200 cc
  6. washwashed twice with an 0.1 N hydrochloric acid solution (a total of 140 cc
  7. dry with material), dried over sodium sulphate
  8. additiontreated with decolourising charcoal
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  11. customThe residue obtained
  12. customA product precipitates which
  13. customis isolated by filtration
  14. customdried under reduced pressure (0.1 mm Hg)

Sources & evidence

ORD record
ord-0bc18ffa12024765b7834d77e0483534
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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