Methyl 3-aminopropanoate hydrochloride → HCID 178424665, compound

HRID 2223751Notes

Reaction equation

HRID 2223751 reaction equation
F[B-](F)(F)F.[CH3:6][C:7]1[C:8]([N+:17]([O-:19])=[O:18])=[C:9]([C:13](=[NH:16])OC)[CH:10]=[CH:11][CH:12]=1.Cl.C[O:22][C:23](=O)[CH2:24][CH2:25][NH2:26].C[O-].[Na+]>CO>[CH3:6][C:7]1[C:8]([N+:17]([O-:19])=[O:18])=[C:9]([C:13]2[NH:26][CH2:25][CH2:24][C:23](=[O:22])[N:16]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 10942334Sodium MethoxideHCID 17960598Methyl 3-methyl-2-nitrobenzenecarboximidate tetrafloroborate

Product 1

HCID 178424665HCID 178424665, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Step B (1.7 g, 5.9 mmol) in methanol (20 mL) was added β-alanine methyl ester hydrochloride (832 mg, 5.9 mmol) followed by sodium methoxide (2.7 mL, 25 wt % in methanol, 11.8 mmol) and the mixture was heated at reflux for 1.5 hour. The mixture was then cooled, stirred overnight at ambient temperature and again heated at reflux for 3 hours. The mixture was then cooled, concentrated and triturated with dichloromethane. The soluble fraction was then purified by flash column chromatography (silica gel, ethyl ether) to give the title compound of Step C as a white solid (0.12 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 hour
  3. temperatureThe mixture was then cooled
  4. temperatureagain heated
  5. temperatureat reflux for 3 hours
  6. temperatureThe mixture was then cooled
  7. concentrationconcentrated
  8. customtriturated with dichloromethane
  9. customThe soluble fraction was then purified by flash column chromatography (silica gel, ethyl ether)

Sources & evidence

ORD record
ord-5abc13b029fa47bda0ac9e03515e7c38
Source dataset
uspto-grants-2008_05
Patent number
US07375232B2

Reaction notes

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