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

HRID 2180774Notes

Reaction equation

HRID 2180774 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 vacua 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 vacua

Sources & evidence

ORD record
ord-2353bf30d22a4ea28061ddd3e989e688
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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