Hydrochloric Acid → HCID 131715598, compound

HRID 580204Notes

Reaction equation

HRID 580204 reaction equation
Cl.[NH2:2][CH:3]1[C:25](=[O:26])[N:5]2[C:6]([C:22]([O-:24])=[O:23])=[C:7](/[CH:10]=[CH:11]/[CH2:12][N+:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[NH2:20])=[CH:15][CH:14]=3)[CH2:8][S:9][C@H:4]12.Cl.[CH2:28]([O:31][N:32]=[C:33]([C:37]1[N:41]=[C:40]([NH2:42])[S:39][N:38]=1)[C:34](Cl)=[O:35])[C:29]#[CH:30].C([O-])([O-])=O.[Na+].[Na+].Cl>CC(C)=O>[NH2:42][C:40]1[S:39][N:38]=[C:37]([C:33](=[N:32][O:31][CH2:28][C:29]#[CH:30])[C:34]([NH:2][CH:3]2[C:25](=[O:26])[N:5]3[C:6]([C:22]([O-:24])=[O:23])=[C:7]([CH:10]=[CH:11][CH2:12][N+:13]4[CH:14]=[CH:15][C:16]([C:19](=[O:21])[NH2:20])=[CH:17][CH:18]=4)[CH2:8][S:9][C@H:4]23)=[O:35])[N:41]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 70416383HCID 70416383, compoundHCID 73663656HCID 73663656, compound

Product 1

HCID 131715598HCID 131715598, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 86 mg (0.19 mmole) of 7-amino-3-[3-(4-carbamoylpyridinio)-1-(E)-propenyl]-3-cephem-4-carboxylate hydrochloride (XXII-H) in 2 ml of 50% aqueous acetone was added 63 mg of 2-propargyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (from Preparation No. 26). The suspension was maintained at pH 6.5-7.0 with 2N Na2CO3 and then stirred at room temperature for 1 hour. The reaction mixture was acidified to pH 2 with 1N HCl and concentrated in vacuo. The residue was diluted with 30 ml of water, neutralized with NaHCO3 and filtered. The filtrate was transferred on the top of a column which was packed with reverse phase carrier (30 ml) taken from a PrepPAK-500/C18 cartridge (Waters). The column was eluted with water, 5% CH3OH, 10% CH3OH and 20% CH3OH, successively. Fractions containing the product were combined and lyophilized to afford 13 mg (12%) of the title product I-4H. Estimated purity 70%. Mp. 160° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 30 ml of water
  3. filtrationfiltered
  4. washThe column was eluted with water, 5% CH3OH, 10% CH3OH and 20% CH3OH
  5. additionFractions containing the product

Sources & evidence

ORD record
ord-ca1cdc98ba63473081919795a9730dde
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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