Hydrochloric Acid → HCID 86133361, compound

HRID 543236Notes

Reaction equation

HRID 543236 reaction equation
[NH2:1][C:2]([C:14]([O:16]C)=[O:15])([CH:11]=[C:12]=[CH2:13])[CH2:3][CH2:4][C:5]([O:7]CC#C)=[O:6].[ClH:18]>>[ClH:18].[NH2:1][C:2]([C:14]([OH:16])=[O:15])([CH:11]=[C:12]=[CH2:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 54524951HCID 54524951, compound

Product 1

HCID 86133361HCID 86133361, compound

Procedure

The hydrolysis of propargyl 4-amino-4-carbomethoxyhepta-5,6-dienoate was carried out by dissolving 360 mg of the diester in 10% HCl and heating the solution to 65°-70° C. for about 22 hours. When cooled, the reaction mixture was placed directly on an ion-exchange column (BioRad Ag 50×8) washed with water, and eluted with a 1.7M ammonium hydroxide solution. The ammonium hydroxide fractions were pooled and concentrated to give the free acid of the title compound which was purified further by passing an aqueous solution of the pyrrolidone through a short column of RP-18 material. Upon concentration of the eluant, a residue was obtained which was taken in a dilute HCl solution of pH 3.2. On evaporation to dryness, the title compound was obtained.

Workup

  1. temperatureheating the solution to 65°-70° C. for about 22 hours
  2. temperatureWhen cooled
  3. washwashed with water
  4. washeluted with a 1.7M ammonium hydroxide solution
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd7c30baecaf4ca28757c122dd0e6e9f
Source dataset
uspto-grants-1987_04
Patent number
US04661510

Reaction notes

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