Triethylamine → Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

HRID 977960Notes

Reaction equation

HRID 977960 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:2]=1.C(N(CC)CC)C.[CH2:22]([O:24][C:25]([CH2:27][C:28](Cl)=[O:29])=[O:26])[CH3:23]>C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:26])[CH2:27][C:28](=[O:29])[N:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 13606577Methyl 3-[(3-pyridinylmethyl)amino]propanoate

Product 1

HCID 53944986Ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetateYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl 3-(3-pyridylmethylamino)propionate (28.72 g), triethylamine (22 ml) and methylene chloride (240 ml) is cooled to 5°-10° C., and thereto is added dropwise a solution of ethoxycarbonylacetyl chloride (23.38 g) in methylene chloride (60 ml). The mixture is stirred at room temperature for one hour. The mixture is filtered to remove precipitates (triethylamine hydrochloride). The filtrate is washed with water, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, ethyl acetate) to give ethyl[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (35.22 g, 77.3%) as oil.

Workup

  1. temperatureis cooled to 5°-10° C.
  2. filtrationThe mixture is filtered
  3. customto remove
  4. customprecipitates (triethylamine hydrochloride)
  5. washThe filtrate is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent, ethyl acetate)

Sources & evidence

ORD record
ord-b10b2e2fd00147b8972c6965c67da6c2
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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