Hydrochloric Acid → HCID 21426475, compound

HRID 258771Notes

Reaction equation

HRID 258771 reaction equation
C(O[CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:24])[CH:10]2[NH:14][C:15](=[O:23])[CH2:16][C:17]2[S:18][C:19](=[O:22])[S:20][CH:21]=2)[C:7]=1[C:25]([OH:27])=[O:26])(=O)C.[CH2:28]([CH:30]1[S:34][C:33](=[S:35])[N:32]=[N:31]1)[CH3:29].Cl>O.C(=O)(O)[O-].[Na+]>[C:25]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:35][C:33]1[S:34][C:30]([CH2:28][CH3:29])=[N:31][N:32]=1)[CH:10]([NH:14][C:15](=[O:23])[CH2:16][C:17]1[S:18][C:19](=[O:22])[S:20][CH:21]=1)[C:9]2=[O:24])([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21426457HCID 21426457, compoundHCID 88827510HCID 88827510, compound

Product 1

HCID 21426475HCID 21426475, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
60 °C

Procedure

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 (7 g.) is dissolved in distilled water (100 cc.) and sodium bicarbonate (1.46 g.). A solution of 5-ethyl-2-thioxo-1,3,4-thiadiazoline (2.63 g.) in distilled water (60 cc.) and sodium bicarbonate (1.46 g.) is added and the resulting solution is heated to 60° C. for 6 hours. After cooling, it is acidified to pH 5.5 by adding 4 N hydrochloric acid and is then extracted twice with ethyl acetate (100 cc.). The organic extracts are discarded. The acidification is continued in the presence of ethyl acetate (300 cc.) until the pH is 2. After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (a total of 200 cc.). The combined organic extracts are washed twice with water (200 cc.), dried over magnesium sulphate, treated with decolourising charcoal and then filtered and concentrated to dryness under reduced pressure (20 mm.Hg). The residue obtained is recrystallised from methanol (100 cc.) to give 2-carboxy-3-[(5-ethyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (2 g.) m.p. 155° C.

Workup

  1. temperatureAfter cooling
  2. extractionis then extracted twice with ethyl acetate (100 cc.)
  3. customAfter decanting the organic phase
  4. extractionthe aqueous phase is extracted twice with ethyl acetate (a total of 200 cc
  5. washThe combined organic extracts are washed twice with water (200 cc.)
  6. dry with materialdried over magnesium sulphate
  7. additiontreated with decolourising charcoal
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  10. customThe residue obtained
  11. customis recrystallised from methanol (100 cc.)

Sources & evidence

ORD record
ord-55e8c97712f64f40aab4a757a24ede8f
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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