Hydrochloric Acid → H-Ala(3-pyridyl)-OMe.2HCl

HRID 636164

Reaction equation

HRID 636164 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([NH:19]C(=O)C)(C(OCC)=O)[C:9]([O:11][CH2:12]C)=[O:10])[CH:2]=1.[ClH:23]>>[ClH:23].[ClH:23].[CH3:12][O:11][C:9](=[O:10])[C@H:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[NH2:19]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13817914Diethyl acetamido[(pyridin-3-yl)methyl]propanedioate

Product 1

HCID 46862166H-Ala(3-pyridyl)-OMe.2HClYield 100%

Procedure

Diethyl 2-(3-pyridylmethyl)-2-acetamidomalonate was dissolved in 6N HCl (30 mL) and heated to reflux for 19 hours whereupon it was cooled to room temperature and the HCl solution was removed by evaporation in vacuo. The intermediate amino acid dihydrochloride salt was taken up into MeOH (30 mL) saturated with HCl gas and stirred for 3.5 hours. The MeOH/HCl was removed by evaporation in vacuo to give 3-(3-pyridyl)alanine methyl ester dihydrochloride (2.235 g, 100%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 19 hours whereupon it
  3. customthe HCl solution was removed by evaporation in vacuo
  4. customThe MeOH/HCl was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-3b4eb682c8a3415d896cf748e834412d
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Linked notes

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