Sodium Hydroxide → HCID 12802218, compound

HRID 257813Notes

Reaction equation

HRID 257813 reaction equation
[NH2:1][C@@H:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9]OC(=O)C)[CH2:7][S:8][C@H:3]12.C(=O)(O)[O-].[Na+].[OH-].[Na+].[N-:26]=[N+:27]=[N-:28].[Na+]>CC(C)=O.O>[NH2:1][C@@H:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][N:26]=[N+:27]=[N-:28])[CH2:7][S:8][C@H:3]12

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12802218HCID 12802218, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylic acid (27.2 g, 99.9 mmol) was added water (500 ml) and sodium bicarbonate (9.3 g, 111 mmol); the pH of the mixture was adjusted to 6.5 with 10% sodium hydroxide solution. Sodium azide (13.1 g, 201 mmol) was added to the mixture followed by acetone (350 ml). The mixture was heated at 60° C. for 6h and left stirring at room temperature overnight. Acetone was removed under reduced pressure and the mixture was cooled in an ice-bath, acidified with concentrated hydrochloric acid to pH 3.5; the precipitated solid was filtered off, dried overnight over P205 to give 14.3 g (56%) of 7β-amino-3-azidomethyl-3-cephem-4-carboxylic acid. IR (Nujol) max 2095, 1796, 1732 cm-1.

Workup

  1. waitleft
  2. customAcetone was removed under reduced pressure
  3. temperaturethe mixture was cooled in an ice-bath
  4. filtrationthe precipitated solid was filtered off
  5. customdried overnight over P205

Sources & evidence

ORD record
ord-489bc51be6294fe9a8abd7443480236c
Source dataset
uspto-grants-1993_11
Patent number
US05264430

Reaction notes

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