Hydrochloric Acid → HCID 178431924, compound

HRID 1448398Notes

Reaction equation

HRID 1448398 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+].Cl.CN(C)CCCN=C=NCC.Cl.[NH2:30][CH:31]1[C:44](=[O:45])[N:33]2[CH:34]([C:39]3[NH:43][N:42]=[N:41][N:40]=3)[C:35]([CH3:38])([CH3:37])[S:36][C@H:32]12.C(C(CCCC)C([O-])=O)C.[Na+]>C(OCC)(=O)C.O>[C:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:11][C:12]([NH:30][CH:31]1[C:44](=[O:45])[N:33]2[CH:34]([C:39]3[NH:40][N:41]=[N:42][N:43]=3)[C:35]([CH3:37])([CH3:38])[S:36][C@H:32]12)=[O:14])([OH:10])=[O:9]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24123o-Phenylenediacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23672331Sodium 2-ethylhexanoateHCID 178431949HCID 178431949, compound

Product 1

HCID 178431924HCID 178431924, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

An ice-bath cooled, stirred mixture of 1.94 g (10 mmol) of o-phenylenediacetic acid, and 60 ml. of water is adjusted to pH 5.5 by the careful addition of 6 N sodium hydroxide. The resulting solution is treated with 1.92 g (10 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and stirring is continued for 30 minutes, with the pH being maintained at 5.5 by the addition of 6.0 N hydrochloric acid. A solution consisting of 2.4 g. (10 mmol) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam and 30 ml. of water (adjusted to pH 7) is added to the first mentioned solution and stirring and cooling is continued for an hour. The aqueous solution is washed three times with 30 ml. portions of ethyl acetate, and is then adjusted to pH 2.5 with 6 N hydrochloric acid. This solution is extracted twice with 40 ml. portions of ethyl acetate, and the combined extracts are washed with 50 ml. of water. After being dried over anhydrous sodium sulfate, the extract is evaporated under reduced pressure to furnish a colorless foam: yield 3 g. The foam is dissolved in 50 ml. of ethyl acetate and then it is treated with 2.4 g. (14.5 mmol) of sodium 2-ethylhexanoate in 30 ml. of ethyl acetate. The title compound precipitates as the sodium salt: yield 3.4 g (74%) IR (KBr) 1770, 1667, and 1587 cm-1NMR (D2O): 7.25 ppm (s, 4H), 5.70 (d, 1H), 5.40 (d, 1H), 5.25 (s, 1H), 3.70 (s, 2H), 3.60 (s, 2H), 1.50 (s, 3H), 1.00 (s, 3H).

Workup

  1. temperatureAn ice-bath cooled
  2. stirringstirring
  3. stirringstirring
  4. temperaturecooling
  5. waitis continued for an hour
  6. washThe aqueous solution is washed three times with 30 ml
  7. extractionThis solution is extracted twice with 40 ml
  8. washportions of ethyl acetate, and the combined extracts are washed with 50 ml
  9. dry with materialAfter being dried over anhydrous sodium sulfate
  10. customthe extract is evaporated under reduced pressure
  11. customto furnish a colorless foam
  12. dissolutionThe foam is dissolved in 50 ml
  13. customThe title compound precipitates as the sodium salt

Sources & evidence

ORD record
ord-cd96496322864a7aa3027f8b70ca1340
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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