Hydrochloric Acid → 4-Amino-5,6-heptadienoic acid

HRID 248206Notes

Reaction equation

HRID 248206 reaction equation
[CH:1]([C@H:4]1[NH:8][C:7](=[O:9])[CH2:6][CH2:5]1)=[C:2]=[CH2:3].Cl.[OH2:11]>>[NH2:8][C@H:4]([CH:1]=[C:2]=[CH2:3])[CH2:5][CH2:6][C:7]([OH:9])=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 45092447(5S)-5-(1,2-Propadienyl)pyrrolidin-2-one

Product 1

HCID 1460904-Amino-5,6-heptadienoic acidYield 80%

Procedure

A solution of (5S)-5-(1,2-propadienyl)pyrrolidin-2-one (37) (1.1 g, 9.0 mmol), 5N HCl (10 mL) and H2O (4 mL) was heated to 80° C. for 18 hours. the solution was cooled, concentrated and neutralized to pH 6 with 1N NaOH. This solution was put on a Dowex 1×2-100 ion exchange column (OH) form. The column was rinsed with distilled H2O (800 mL) and the compound was removed with 0.5N acetic acid. Lyophilization gave (4S)-4-amino-5,6-heptadienoic acid as an off-white foamy solid (1.01 g, 80%).

Workup

  1. temperaturethe solution was cooled
  2. concentrationconcentrated
  3. washThe column was rinsed with distilled H2O (800 mL)
  4. customthe compound was removed with 0.5N acetic acid

Sources & evidence

ORD record
ord-ba1c8c32c13a460f93b4868f027bf2c8
Source dataset
uspto-grants-1993_05
Patent number
US05208345

Reaction notes

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