Hydrochloric Acid → HCID 131711642, compound

HRID 426817Notes

Reaction equation

HRID 426817 reaction equation
C([NH+](CC)CC)C.[CH2:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]([CH:20]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:21]([NH:23][CH:24]3[C:35](=[O:36])[N:26]4[CH:27]([C:32]([O-:34])=[O:33])[C:28]([CH3:31])([CH3:30])[S:29][C@H:25]34)=[O:22])=[O:19])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.C(OCC)(=O)C.Cl.C(C(CC)C([O-])=O)C.[Na+:58]>CC(C)=O>[Na+:58].[CH2:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]([CH:20]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:21]([NH:23][CH:24]3[C:35](=[O:36])[N:26]4[CH:27]([C:32]([O-:34])=[O:33])[C:28]([CH3:30])([CH3:31])[S:29][C@H:25]34)=[O:22])=[O:19])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23663635Sodium 2-ethylbutyrateHCID 131711636HCID 131711636, compound

Product 1

HCID 131711642HCID 131711642, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 25 g. (0.048 moles) of 6-(α-[5-indanyloxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt in 150 ml. of ethyl acetate is cooled to 0° C., and the suspension is acidified with 2 n aqueous hydrochloric acid (18 ml.) to pH=2. The organic phase is separated and the aqueous-acidic phase is extracted with 2×20 ml. of ethyl acetate. The organic solutions are combined, washed with 3×30 ml. of saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and neutralized with a solution of 6.7 g. (0.048 moles) of sodium diethylacetate in 30 ml. of acetone. About 50% of the solvent is evaporated in vacuo. 100 ml. of diisopropyl ether are added to the concentrate, the mixture is cooled, and the obtained white, powdery substance is filtered off. 18 g. (80%) of 6-(α-[5-indanyloxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid sodium salt are obtained; m.p.:b 220°-222° C.

Workup

  1. additionA suspension of 25 g
  2. customThe organic phase is separated
  3. extractionthe aqueous-acidic phase is extracted with 2×20 ml
  4. washwashed with 3×30 ml
  5. dry with materialof saturated aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. customAbout 50% of the solvent is evaporated in vacuo
  8. additionof diisopropyl ether are added to the concentrate
  9. temperaturethe mixture is cooled
  10. filtrationthe obtained white, powdery substance is filtered off

Sources & evidence

ORD record
ord-0a285c0be7c24dcc81bc85782eb62856
Source dataset
uspto-grants-1979_10
Patent number
US04171303

Reaction notes

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