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

HRID 1533607Notes

Reaction equation

HRID 1533607 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-5b5d7a85623f46b38fe400400373da8b
Source dataset
uspto-grants-2001_03
Patent number
US06207710B1

Reaction notes

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