Hydrochloric Acid → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetamido]-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate

HRID 580205Notes

Reaction equation

HRID 580205 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.[NH2:28][C:29]1[S:33][N:32]=[C:31]([C:34](=[N:38][O:39][CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)[C:35](Cl)=[O:36])[N:30]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>CC(C)=O>[NH2:28][C:29]1[S:33][N:32]=[C:31]([C:34](=[N:38][O:39][CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)[C:35]([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:36])[N:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 736636582-(5-Amino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetyl chloride hydrochlorideHCID 1317155967-Amino-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 1317156007-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetamido]-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 139 mg (0.31 mmole) of 7-amino-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate hydrochloride in 3.5 ml of 50% aqueous acetone in an ice-cooling bath was added portionwise 120 mg (0.44 mmole) of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetyl chloride hydrochloride (from Preparation No. 27). The mixture was adjusted to pH 6.5-7.0 with 2N Na2CO3 (0.9 ml) and stirred for 1 hour at 10° C. The reaction mixture was acidified to pH 2 with 1N HCl and evaporated under reduced pressure. The residue was chromatographed on a column of HP-20 resin (20 ml) and was eluted with 300 ml of water and 30% CH3OH-H2O, successively. Fractions containing the product were combined and concentrated in vacuo. The residue was treated with 60 ml of acetone to give 111 mg (83 %) of the title compound I-5H. Mp. 160° C. (dec.). Estimated purity 70%.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was chromatographed on a column of HP-20 resin (20 ml)
  3. washwas eluted with 300 ml of water and 30% CH3OH-H2O
  4. additionFractions containing the product
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with 60 ml of acetone

Sources & evidence

ORD record
ord-23b5f812b2b64ce1917f952996898939
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

Loading…