Hydrochloric Acid → Disodium

HRID 1833428Notes

Reaction equation

HRID 1833428 reaction equation
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([P:10]([OH:14])([O:12][CH3:13])=[O:11])[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.[OH-].[Na+:18].[C:19]1([CH:25]([C:29](O)=[O:30])[C:26]([OH:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C.Cl.C(=O)([O-])O.[Na+:49].C(C(CCCC)C([O-])=O)C.[Na+]>C(OCC)(=O)C.O>[Na:18][Na:49].[C:26]([CH:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:29]([NH:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([P:10]([OH:14])([O:12][CH3:13])=[O:11])[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]12)=[O:30])([OH:28])=[O:27]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 75791Phenylmalonic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23672331Sodium 2-ethylhexanoateHCID 867348606-amino-2,2-dimethyl-3-(O-methylphosphono)penam

Product 2

HCID 141233DisodiumHCID 867353296-(2-carboxy-2-phenylacetamido)-2,2-dimethyl-3-(O-methylphosphono)penam

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 266 mg. (0.001 mole ) of 6-amino-2,2-dimethyl-3-(O-methylphosphono)penam in 8 ml. of water is added dropwise dilute aqueous sodium hydroxide to obtain a pH of 6.1. To this solution is then added 235 mg. (0.0013 mole) of phenylmalonic acid, followed by 190 mg. (0.001 mole) of 1-ethyl-3-(3-dimethylaminoprop-1-yl)carbodiimide hydrochloride. The solution is stirred for 3.5 hours, during which time the pH is maintained in the range from 6.1 to 6.3 by the dropwise addition of dilute hydrochloric acid. At this point, the pH is raised to 7.3 by the addition of saturated sodium hydrogen carbonate solution, and the reaction mixture is washed with ethyl acetate. The wash is discarded. The aqueous phase is then adjusted to pH 2 using dilute hydrochloric acid, and then it is extracted twice with 30 ml. portions of ethyl acetate. The combined extracts are dried, and concentrated to a volume of about 25 ml. To this solution is added a solution of 330 mg. (0.002 mole) of sodium 2-ethylhexanoate in 2.0 ml. of ethyl acetate. The precipitate which forms is filtered to give the disodium salt of 6-(2-carboxy-2-phenylacetamido)-2,2-dimethyl-3-(O-methylphosphono)penam.

Workup

  1. customto obtain a pH of 6.1
  2. additionTo this solution is then added 235 mg
  3. washthe reaction mixture is washed with ethyl acetate
  4. extractionit is extracted twice with 30 ml
  5. customThe combined extracts are dried
  6. concentrationconcentrated to a volume of about 25 ml
  7. additionTo this solution is added a solution of 330 mg
  8. filtrationThe precipitate which forms is filtered

Sources & evidence

ORD record
ord-44b99c1932404269bde6cd075cb3dc4a
Source dataset
uspto-grants-1978_01
Patent number
US04066657

Reaction notes

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