Triethylamine → HCID 131710863, compound

HRID 66105Notes

Reaction equation

HRID 66105 reaction equation
N1C=C[C:4]([S:7]CC(Cl)=O)=[CH:3][CH:2]=1.[NH2:12][CH:13]1[C:35](=[O:36])[N:15]2[C:16]([C:32]([OH:34])=[O:33])=[C:17]([CH2:20][S:21][C:22]3[O:23][C:24]([CH2:27][S:28]([OH:31])(=[O:30])=[O:29])=[N:25][N:26]=3)[CH2:18][S:19][C@H:14]12.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C>CN(C)C=O>[N:39]1[CH:40]=[CH:41][C:2]([CH2:3][C:4]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:32]([OH:34])=[O:33])=[C:17]([CH2:20][S:21][C:22]4[O:23][C:24]([CH2:27][S:28]([OH:31])(=[O:29])=[O:30])=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[S:7])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104376(4-Pyridylthio)acetyl chlorideHCID 887965437-Amino-3-(5-sulfomethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 131710863HCID 131710863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Pyridylthio)acetyl chloride (0.53 g, 2.8 mmol) is dropwise added to a mixture of 1.0 g of 7-amino-3-(5-sulfomethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid and 0.9 g (9.0 mmol) of triethylamine in 10 ml of dry dimethylformamide. The reaction mixture is stirred for 1.5 hour at -10°, then it is warmed to ambient temperature and stirred for 1 hour. The mixture is filtered and the filtrate is diluted with 200 ml of ether-petroleum ether. The precipitate is collected by filtration and dissolved in water. The aqueous solution is passed through an Amberlite IR-120H resin column and the product-containing fractions are lyophilized to give the title compound.

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe mixture is filtered
  3. additionthe filtrate is diluted with 200 ml of ether-petroleum ether
  4. filtrationThe precipitate is collected by filtration
  5. dissolutiondissolved in water

Sources & evidence

ORD record
ord-21678636afc0497ba060b2519240e59f
Source dataset
uspto-grants-1978_12
Patent number
US04130644

Reaction notes

Loading…