Triethylamine → N-butyloxycarbonyl-amino malonic acid diethyl ester

HRID 487335Notes

Reaction equation

HRID 487335 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:11])[CH:6]([NH2:10])[C:7]([OH:9])=[O:8])[CH3:3].[CH2:12]([O:16][C:17](Cl)=[O:18])[CH2:13][CH2:14][CH3:15].[CH2:20](N(CC)CC)[CH3:21]>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:11])[CH:6]([NH:10][C:17]([O:16][CH2:12][CH2:13][CH2:14][CH3:15])=[O:18])[C:7]([O:9][CH2:20][CH3:21])=[O:8])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 20464734Ethyl aminomalonate hydrochloride

Product 1

HCID 21805915N-butyloxycarbonyl-amino malonic acid diethyl esterYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To an ice-cold suspension of 15 g (70.87 mmol) of amino malonic acid ethyl ester hydrochloride in 180 ml of methylene chloride, 10.8 g (75 mmol) of chloroformic acid butyl ester and then 14.7 g (145 mmol) of triethylamine were added within several minutes. In this case the temperature was constantly maintained under 20° C. After the addition was completed, the reaction was stirred for another 75 minutes at room temperature. The reaction solution was diluted with 80 ml of CH2Cl2, washed with two portions of water, and dried on Na2SO4. After concentration by evaporation on a rotary evaporator, 18.8 g (96 percent) of pure title product was obtained. Other data concerning the product was:

Workup

  1. additionAfter the addition
  2. washwashed with two portions of water
  3. customdried on Na2SO4
  4. concentrationAfter concentration
  5. customby evaporation
  6. customon a rotary evaporator

Sources & evidence

ORD record
ord-b322bd32afe2486a89381f5cb94636c0
Source dataset
uspto-grants-1994_03
Patent number
US05294710

Reaction notes

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