Hydrochloric Acid → 7-(alpha-Carboxythien-2-ylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid disodium salt

HRID 971503Notes

Reaction equation

HRID 971503 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]([OH:12])=[O:11])[C:7]([OH:9])=[O:8].C(=O)(O)[O-].[Na+:17].[NH2:18][CH:19]1[C:37](=[O:38])[N:21]2[C:22]([C:34]([OH:36])=[O:35])=[C:23]([CH2:26][S:27][C:28]3[N:32]([CH3:33])[N:31]=[N:30][N:29]=3)[CH2:24][S:25][C@H:20]12.Cl.CN(C)CCCN=C=NCC.Cl>O>[Na+:17].[Na+:17].[C:10]([CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]([NH:18][CH:19]1[C:37](=[O:38])[N:21]2[C:22]([C:34]([O-:36])=[O:35])=[C:23]([CH2:26][S:27][C:28]3[N:32]([CH3:33])[N:31]=[N:30][N:29]=3)[CH2:24][S:25][C@H:20]12)=[O:9])([OH:12])=[O:11].[C:7]([CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:10]([NH:18][CH:19]1[C:37](=[O:38])[N:21]2[C:22]([C:34]([O-:36])=[O:35])=[C:23]([CH2:26][S:27][C:28]3[N:32]([CH3:33])[N:31]=[N:30][N:29]=3)[CH2:24][S:25][C@H:20]12)=[O:11])([OH:9])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 15607089(Thiophen-2-yl)propanedioic acid

Product 1

HCID 1317115557-(alpha-Carboxythien-2-ylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid disodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of thien-2-ylmalonic acid (0.93 g., 0.005 M) in water (25 ml.) was adjusted to pH 6.0 with saturated sodium bicarbonate solution, 7-amino-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid was added, the solution again adjusted to 6.0, cooled to 0° and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.01 g., 0.005 M) added. The mixture was maintained at pH 5.8-6.0 with 6 N hydrochloric acid for two hours at room temperature then saturated sodium bicarbonate was added to pH 7.7 and the solution washed with ethyl acetate (50 ml.). The solution was acidified to pH 4.0, washed with ethyl acetate (2×25 ml.), acidified to pH 2.0 and extracted with ethyl acetate (2×50 ml.), The extracts were washed with water (25 ml.) and brine (25 ml.), dried over anhydrous magnesium sulphate, treated with 2 N sodium 2-ethylhexoate in methylisobutylketone (2 ml.), diluted with ether (200 ml.) and the precipitated disodium salt collected and dried in vacuo. Yield 1.16 g., 43.0%; U.V. spectrum (95% ethanol), λmax (ε=8.250). Paper chromatography (butanol/ethanol/water) showed a zone at Rf =0.05.

Workup

  1. additionwas added
  2. temperaturecooled to 0°
  3. washthe solution washed with ethyl acetate (50 ml.)
  4. washwashed with ethyl acetate (2×25 ml.)
  5. extractionextracted with ethyl acetate (2×50 ml.)
  6. washThe extracts were washed with water (25 ml.) and brine (25 ml.)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. additiontreated with 2 N sodium 2-ethylhexoate in methylisobutylketone (2 ml.)
  9. additiondiluted with ether (200 ml.)
  10. customthe precipitated disodium salt collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-92ce9f02217a4b9e8ed22c95d888c793
Source dataset
uspto-grants-1979_07
Patent number
US04160086

Reaction notes

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