Sodium Nitrite → HCID 178507972, compound

HRID 1065851Notes

Reaction equation

HRID 1065851 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:30]=[N:31][N:32]=2)[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH2:11][S:12][C@@H:13]3[CH:20]([NH:21][C:22](=[O:28])[CH2:23][C:24](=[O:27])[CH2:25][Cl:26])[C:19](=[O:29])[N:14]3[C:15]=2[C:16]([OH:18])=[O:17])[CH:7]=1.[N:33]([O-])=[O:34].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[C:3]2[N:4]([N:30]=[N:31][N:32]=2)[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH2:11][S:12][C@@H:13]3[CH:20]([NH:21][C:22](=[O:28])[C:23](=[N:33][OH:34])[C:24](=[O:27])[CH2:25][Cl:26])[C:19](=[O:29])[N:14]3[C:15]=2[C:16]([OH:18])=[O:17])[CH:7]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 1317127263-[(8-Amino-6-tetrazolo[1,5-b]pyridazinyl)-thiomethyl]-7-(4-chloro-3-oxobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 178507972HCID 178507972, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-[(8-amino-6-tetrazolo[1,5-b]pyridazinyl)thiomethyl]-7-(4-chloro-3-oxobutyramido)-3-cephem-4-carboxylic acid (6.72 g; 0.0171 mole) in acetic acid (60 ml), a solution of sodium nitrite (1.65 g; 0.0239 mole) in water (6 ml) was added at 5°-10° C. After stirring for 3.5 hours at room temperature, the reaction mixture was quenched with brine and extracted with ethyl acetate (4×200 ml). The combined extracts were washed with water, dried over NaSO4 and evaporated to a foam. Trituration of this product with diethyl ether afforded the title compound as a beige powder, 6.3 g.

Workup

  1. customthe reaction mixture was quenched with brine
  2. extractionextracted with ethyl acetate (4×200 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialdried over NaSO4
  5. customevaporated to a foam

Sources & evidence

ORD record
ord-bfb8ae8e33b84704a95ddada19572fdc
Source dataset
uspto-grants-1982_05
Patent number
US04331666

Reaction notes

Loading…