Hydrochloric Acid → HCID 21426449, compound

HRID 258705Notes

Reaction equation

HRID 258705 reaction equation
C(O[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][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:24])=[O:23])[C:7]=1[C:27]([OH:29])=[O:28])(=O)C.C(=O)(O)[O-].[Na+].[CH3:35][C:36]1[S:37][C:38](=[S:41])[NH:39][N:40]=1.Cl>O>[C:27]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:41][C:38]1[S:37][C:36]([CH3:35])=[N:40][N:39]=1)[CH:10]([NH:14][C:15](=[O:25])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22]([CH3:24])=[O:23])[C:9]2=[O:26])([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426442HCID 21426442, compound

Product 1

HCID 21426449HCID 21426449, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

3-Acetoxymethyl-2-carboxy-7-[(2-methylsulphinylimidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]-oct-2-ene (8.5 g.) and sodium bicarbonate (1.62 g.) are dissolved in water (75 cc.). A solution of 2-methyl-5-thioxo-1,3,4-thiadiazoline (2.54 g.) and sodium bicarbonate (1.62 g.) in water (75 cc.) is added and the mixture is heated at 60° C. for 6 hours. After cooling, the pH is adjusted to 6 by adding hydrochloric acid (4 N) and the mixture is washed twice with ethyl acetate (a total of 200 cc.). The mixture is acidified to pH 2 by adding hydrochloric acid (4 N); a product precipitates and is filtered off and dried under reduced pressure (1 mm.Hg) to give 7.9 g. of product. Recrystallisation from methanol (25 cc.), filtration and drying under reduced pressure (0.1 mm.Hg) gives 2-carboxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-7-[(2-methylsulphinyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (2.7 g.), m.p. 227° C. (with decomposition), [α]D20 = -35° ± 1° (c= 1, dimethylformamide).

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed twice with ethyl acetate (a total of 200 cc
  3. additionby adding hydrochloric acid (4 N)
  4. customa product precipitates
  5. filtrationis filtered off
  6. customdried under reduced pressure (1 mm.Hg)
  7. customto give 7.9 g
  8. customRecrystallisation
  9. filtrationfrom methanol (25 cc.), filtration
  10. customdrying under reduced pressure (0.1 mm.Hg)

Sources & evidence

ORD record
ord-a4e1b44022af4feaa72a302e5bdb4dc0
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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