Methyl 3-aminopropanoate hydrochloride → HCID 178424665, compound

HRID 1866768Notes

Reaction equation

HRID 1866768 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-f40d8ef265e141e39d27ebe2077bcc18
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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