Sodium Nitrite → HCID 178494569, compound

HRID 1153780Notes

Reaction equation

HRID 1153780 reaction equation
[Cl:1][CH2:2][C:3](=[O:31])[CH2:4][C:5]([NH:7][CH:8]1[C:29](=[O:30])[N:10]2[C:11]([C:18]([O:20][CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:19])=[C:12]([CH2:15][O:16][CH3:17])[CH2:13][S:14][C@H:9]12)=[O:6].[N:32]([O-])=[O:33].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][CH2:2][C:3](=[O:31])[C:4](=[N:32][OH:33])[C:5]([NH:7][CH:8]1[C:29](=[O:30])[N:10]2[C:11]([C:18]([O:20][CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:26])([CH3:27])[CH3:25])=[O:19])=[C:12]([CH2:15][O:16][CH3:17])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 88659654HCID 88659654, compound

Product 1

HCID 178494569HCID 178494569, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.57 g of pivaloyloxymethyl 7-(4-chloro-3-oxobutyrylamino)-3-methoxymethyl-3-cephem-4-carboxylate were dissolved in 25 ml of acetic acid, and then 409 mg of sodium nitrite were added, little by little, at room temperature to the solution, after which the mixture was stirred for 30 minutes. The mixture was then diluted with 200 ml of ethyl acetate, washed three times with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure. The residue was twice subjected to azeotropic distillation using toluene and the resulting residue was dried, giving 2.7 g of the title compound as a foamy solid.

Workup

  1. washwashed three times with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulphate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. distillationThe residue was twice subjected to azeotropic distillation
  5. customthe resulting residue was dried

Sources & evidence

ORD record
ord-aa19cb748d9949078ab4e5fd548f9e1d
Source dataset
uspto-grants-1984_12
Patent number
US04486425

Reaction notes

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