Hydrochloric Acid → Methyl 3-amino-2-(aminomethyl)propanoate--hydrogen chloride (1/2)

HRID 2357195Notes

Reaction equation

HRID 2357195 reaction equation
[Na].[C:2]([CH:4]([C:9]#[N:10])[C:5]([O:7][CH3:8])=[O:6])#[N:3].[ClH:11]>[Pd].CO>[ClH:11].[ClH:11].[NH2:3][CH2:2][CH:4]([CH2:9][NH2:10])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 10931428HCID 10931428, compound

Product 1

HCID 71720940Methyl 3-amino-2-(aminomethyl)propanoate--hydrogen chloride (1/2)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirring suspension of 10% palladium on carbon (2.0 g) in a solution of the sodium salt of methyl dicyanoacetate (1.00 g, 6.20 mmol) in methanol (100 mL) containing concd hydrochloric acid (32%, 2.0 mL) was hydrogenated at 5 bar and rt. for 24 h. The catalyst was removed by filtration and the solvent was evaporated in vacuo. The residue was treated with methanol (50 mL) and the precipitated sodium chloride was removed by filtration. The solution was concentrated to a low volume in vacuo and then EtOAc was added to precipitate the bis-hydrochloride 12 as an off-white solid (1.20 g).

Workup

  1. customwas hydrogenated at 5 bar and rt
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated in vacuo
  4. additionThe residue was treated with methanol (50 mL)
  5. customthe precipitated sodium chloride was removed by filtration
  6. concentrationThe solution was concentrated to a low volume in vacuo
  7. additionEtOAc was added
  8. customto precipitate the bis-hydrochloride 12 as an off-white solid (1.20 g)

Sources & evidence

ORD record
ord-d34920a17b1f477aa587b03d527648c2
Source dataset
uspto-grants-2010_07
Patent number
US07759519B2

Reaction notes

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