Phosphoric Acid → HCID 70582695, compound

HRID 28018Notes

Reaction equation

HRID 28018 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([O-:20])=[O:19])=[C:13]([CH2:16][OH:17])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[C:24]([N:29]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[S:30]1(=[O:32])=[O:31])([O:26][CH2:27][CH3:28])=[O:25].C(N(CC)CC)C.P(=O)(O)(O)O>CN(C)C=O.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH2:16][O:17][C:39](=[O:40])[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:30](=[O:32])(=[O:31])[NH:29][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 8471Triethylamine2×HCID 227704Ethyl 3-oxo-1,2-benzothiazole-2(3h)-carboxylate 1,1-dioxideHCID 70582610Sodium 7beta-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate

Product 1

HCID 70582695HCID 70582695, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In dimethylformamide (20 ml) is dissolved sodium 7β-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate (3.20 g), followed by the addition of N-carboethoxysaccharin (3.20 g) and triethylamine (2.0 ml). The solution is stirred for one hour at room temperature and, after the addition of triethylamine (2.0 ml), stirred further for one hour. The solution is poured into toleune (1 L) and the resultant precipitate is collected by filtration, washed with toleune and dried. The powder thus obtained is dissolved in water (30 ml). After the addition of ethyl acetate (200 ml), the solution is adjusted to pH 4.0 with diluted phosphoric acid. After separation, the ethyl acetate solution is washed with water, dried over anhydrous sodium sulfate and concentrated. To the concentrate (30 ml), ether (200 ml) is added under stirring and the resultant precipitate is filtered off. The filtrate is concentrated under reduced pressure and to the concentrate (30 ml) is added carbon tetrachloride (100 ml). The resultant precipitate is collected by filtration, washed with carbon tetrachloride and dried over phosphorus pentoxide. The procedure provides 7β-(t-butoxycarbonyl)amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (2.50 g).

Workup

  1. stirringstirred further for one hour
  2. additionThe solution is poured into toleune (1 L)
  3. filtrationthe resultant precipitate is collected by filtration
  4. washwashed with toleune
  5. customdried
  6. customThe powder thus obtained
  7. customAfter separation
  8. washthe ethyl acetate solution is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. concentrationTo the concentrate (30 ml), ether (200 ml)
  12. additionis added
  13. stirringunder stirring
  14. filtrationthe resultant precipitate is filtered off
  15. concentrationThe filtrate is concentrated under reduced pressure
  16. concentrationto the concentrate (30 ml)
  17. additionis added carbon tetrachloride (100 ml)
  18. filtrationThe resultant precipitate is collected by filtration
  19. washwashed with carbon tetrachloride
  20. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-83e2b0c033364b3a9d8de1932c834bd9
Source dataset
uspto-grants-1980_09
Patent number
US04224441

Reaction notes

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