Triethylamine → HCID 131715121, compound

HRID 977969Notes

Reaction equation

HRID 977969 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:18])[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH2:26]([O:28][C:29]([CH2:31][C:32](Cl)=[O:33])=[O:30])[CH3:27]>C(Cl)Cl>[CH2:26]([O:28][C:29](=[O:30])[CH2:31][C:32](=[O:33])[N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:18])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 70434271HCID 70434271, compound

Product 1

HCID 131715121HCID 131715121, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(p-Nitrobenzyl)-β-alanine methyl ester hydrochloride (32.66 g) and triethylamine (38 ml) are dissolved in methylene chloride (200 ml), and a solution of ethoxycarbonylacetyl chloride (20.0 g) in methylene chloride (100 ml) is added dropwise to the mixture under ice-cooling. The mixture is stirred at the same temperature for one hour, and the mixture is filtered to remove precipitates (triethylamine hydrochloride). The filtrate is washed with 2% HCl, water, 2% NaOH and water, dried and then distilled to remove the solvent to give ethyl[N-(p-nitrobenzyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (40.4 g, 96.4%) as yellow oil.

Workup

  1. temperaturecooling
  2. filtrationthe mixture is filtered
  3. customto remove
  4. customprecipitates (triethylamine hydrochloride)
  5. washThe filtrate is washed with 2% HCl, water, 2% NaOH and water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent

Sources & evidence

ORD record
ord-75c6abd85a0d4bfbbd0500dcd88f0964
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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