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

HRID 580203Notes

Reaction equation

HRID 580203 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:30][N:31]=[C:32]([C:36]1[N:40]=[C:39]([NH2:41])[S:38][N:37]=1)[C:33](Cl)=[O:34])[CH3:29].C([O-])([O-])=O.[Na+].[Na+].Cl>CC(C)=O>[NH2:41][C:39]1[S:38][N:37]=[C:36]([C:32](=[N:31][O:30][CH2:28][CH3:29])[C:33]([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:34])[N:40]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 867392542-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochlorideHCID 1317155967-Amino-3-[3-(4-carbamoylpyridinio)-1-propenyl]-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 1317155947-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[3-(4-carbamoylpyridinio)-1-propen-1-yl]-3-cephem-4-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 200 mg of 7-amino-3-[3-(4-carbamoylpyridinio)-1-propen-1-yl]-3-cephem-4-carboxylate hydrochloride (E isomer) in 5 ml of 50% aqueous acetone was added portionwise 190 mg of 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride [prepared according to the procedure described in published Japan patent application (Kokai) No. 57-24389 (2/8/82)], and the mixture was adjusted to pH 6.5-7.0 with 2N Na2CO3 (about 1 ml). The reaction mixture was stirred at 10° C. for an hour, acidified to pH 2 with 1N HCl and evaporated in vacuo. The residue was filtered and the filtrate was chromatographed on a column of HP-20, which was eluted with 500 ml of water and 25% aqueous isopropanol, successively. Fractions containing the desired product were combined and evaporated under reduced pressure. The oily residue was treated with isopropanol (20 ml) to give 263 mg (93%) of the title compound (I-2H). M.p. 170° C. (dec.).

Workup

  1. customprepared
  2. customevaporated in vacuo
  3. filtrationThe residue was filtered
  4. customthe filtrate was chromatographed on a column of HP-20, which
  5. washwas eluted with 500 ml of water and 25% aqueous isopropanol
  6. additionFractions containing the desired product
  7. customevaporated under reduced pressure
  8. additionThe oily residue was treated with isopropanol (20 ml)

Sources & evidence

ORD record
ord-c368a0f54c474b5aa7c55b7acdfc707d
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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