Hydrochloric Acid → HCID 21426456, compound

HRID 258778Notes

Reaction equation

HRID 258778 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.[CH3:28][C:29]1[CH2:33][S:32][C:31](=[S:34])[N:30]=1.Cl.C(OC(C)C)(C)C>O.C(=O)(O)[O-].[Na+].CO>[C:25]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:34][C:31]1[S:32][CH:33]=[C:29]([CH3:28])[N:30]=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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 21426457HCID 21426457, compoundHCID 23055737HCID 23055737, compound

Product 1

HCID 21426456HCID 21426456, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 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 (7.7 g.) is dissolved in distilled water (100 cc.) and sodium bicarbonate (1.64 g.). A solution of 4-methyl-2-thioxo-1,3-thiazoline (2.76 g.) in distilled water (75 cc.) and sodium bicarbonate (1.64 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 then extracted with ethyl acetate (100 cc.), which is discarded. The acidification is continued to pH 2 in the presence of ethyl acetate (300 cc.). After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (a total of 200 cc.). The 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 dissolved in methanol (30 cc.) and this solution is then added to isopropyl ether (200 cc.). A product precipitates and is isolated by filtration to give 2-carboxy-3-[(4-methyl-1,3-thiazol-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.).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (100 cc.), which
  3. customAfter decanting the organic phase
  4. extractionthe aqueous phase is extracted twice with ethyl acetate (a total of 200 cc
  5. washThe 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. customA product precipitates
  12. customis isolated by filtration

Sources & evidence

ORD record
ord-ede00b3377ba497dad244cc99d8f9950
Source dataset
uspto-grants-1977_07
Patent number
US04034090

Reaction notes

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