24209-38-9 → HCID 21426443, compound

HRID 258701Notes

Reaction equation

HRID 258701 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1[N:20]([CH3:21])[N:19]=[N:18][N:17]=1)=[C:7]2[C:11]([OH:13])=[O:12].[S:22]([C:26]1[N:27]([CH2:31][C:32](Cl)=[O:33])[CH:28]=[CH:29][N:30]=1)([CH3:25])(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>O.[Na].CC(C)=O>[C:11]([C:7]1[N:8]2[CH:3]([S:4][CH2:5][C:6]=1[CH2:14][S:15][C:16]1[N:20]([CH3:21])[N:19]=[N:18][N:17]=1)[CH:2]([NH:1][C:32](=[O:33])[CH2:31][N:27]1[CH:28]=[CH:29][N:30]=[C:26]1[S:22]([CH3:25])(=[O:24])=[O:23])[C:9]2=[O:10])([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 9113624209-38-9HCID 516892Sodium Bicarbonate2×HCID 21426439HCID 21426439, compound

Product 1

HCID 21426443HCID 21426443, compoundYield 3.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 5360545SodiumSolvent

Conditions

Temperature
4 °C

Procedure

Acetone (200 cc.) is added to a solution of 7-amino-2-carboxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (18.4 g.) in water (110 cc.) and sodium bacarbonate (9.41 g). The mixture is cooled to about 4° C., and (2-mesyl-imidazol-1-yl)-acetyl chloride (12.4 g.) in acetone (50 cc.) is added dropwise while keeping the pH at 7 by adding a saturated aqueous solution of sodium bicarbonate. After having allowed reaction to take place for 1 hour, the acetone is removed under reduced pressure (20 mm.Hg). The pH is brought to 2.5 by adding 6 N hydrochloric acid; a solid precipitates. Ethyl acetate (100 cc.) is added, the mixture is stirred, and then the solid is filtered off and washed with ethyl acetate (500 cc.). The combined organic filtrates are dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm.Hg). A residue (8.7 g.) is obtained and is taken up in a saturated aqueous solution of sodium bicarbonate (100 cc.). The aqueous phase is washed with ethyl acetate (100 cc.) and then acidified to pH 5 by adding 6 N hydrochloric acid; a slight amount of insoluble matter is filtered off and then the filtrate is acidified to pH 2.5: a product precipitates. Extraction is effected using ethyl acetate (800 cc.), and the organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm.Hg). The residue is stirred with acetonitrile (40 cc.) and the solid formed is collected to yield 2-carboxy-7-[(2-mesyl-imidazol-1-yl)-acetamido] -3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene (1.08 g.), m.p. approx. 230° C., [α]D20 = -42°± 1 (c= 0.87, dimethylformamide).

Workup

  1. customreaction
  2. customfor 1 hour
  3. customthe acetone is removed under reduced pressure (20 mm.Hg)
  4. additionby adding 6 N hydrochloric acid
  5. customa solid precipitates
  6. additionEthyl acetate (100 cc.) is added
  7. filtrationthe solid is filtered off
  8. washwashed with ethyl acetate (500 cc.)
  9. dry with materialThe combined organic filtrates are dried over sodium sulphate
  10. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  11. customA residue (8.7 g.) is obtained
  12. washThe aqueous phase is washed with ethyl acetate (100 cc.)
  13. additionby adding 6 N hydrochloric acid
  14. filtrationa slight amount of insoluble matter is filtered off
  15. customa product precipitates
  16. extractionExtraction
  17. dry with materialthe organic extracts are dried over sodium sulphate
  18. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  19. stirringThe residue is stirred with acetonitrile (40 cc.)
  20. customthe solid formed
  21. customis collected

Sources & evidence

ORD record
ord-912a28da904146238a6c58d4b5c77c05
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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