Sodium Hydroxide → Sodium 7beta-(2-methylsulfonylethoxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate

HRID 1649758Notes

Reaction equation

HRID 1649758 reaction equation
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]12.[OH-].[Na+:17].C(=O)([O-])O.[Na+].[CH3:23][S:24]([CH2:27][CH2:28][O:29][C:30](Cl)=[O:31])(=[O:26])=[O:25]>O.O1CCCC1>[CH3:23][S:24]([CH2:27][CH2:28][O:29][C:30]([NH:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([O-:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]12)=[O:31])(=[O:26])=[O:25].[Na+:17]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 104458Carbonochloridic acid, 2-(methylsulfonyl)ethyl esterHCID 516892Sodium BicarbonateHCID 11031679(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Product 1

HCID 67868135Sodium 7beta-(2-methylsulfonylethoxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of water is suspended 4.60 g of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid and, with ice-cooling and stirring, 20 ml of 1N aqueous sodium hydroxide solution is added to the suspension for dissolving the acid. To the solution is added 1.85 g of sodium hydrogen carbonate and, then, a solution of 4.11 g of 2-methylsulfonylethoxycarbonyl chloride in 40 ml of tetrahydrofuran is added dropwise. The mixtrue is stirred with ice-cooling for 2 hours, then adjusted to pH 6.5, washed with ethyl acetate, and concentrated under reduced pressure. The residue is subjected to column chromatography on XAD-II (600 ml). Elution is performed with water and the eluate is concentrated under reduced pressure and freeze-dried to give 3.10 g of sodium 7β-(2-methylsulfonylethoxycarbonylamino)-3-hydroxymethyl-3-cephem-4-carboxylate as light yellow powders.

Workup

  1. temperaturewith ice-cooling
  2. dissolutionfor dissolving the acid
  3. stirringThe mixtrue is stirred with ice-
  4. temperaturecooling for 2 hours
  5. washwashed with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. washElution
  8. concentrationthe eluate is concentrated under reduced pressure
  9. customfreeze-dried

Sources & evidence

ORD record
ord-99c18f30ea1e46b09e7d193242ee47b9
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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