Hydrochloric Acid → diethyl(acetylamino)(hexadecyl)propanedioate

HRID 617823Notes

Reaction equation

HRID 617823 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82131-BromohexadecaneHCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 227970diethyl(acetylamino)(hexadecyl)propanedioateYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.13 g of sodium ethoxide was added thereto. A solution of 5.5 g of hexadecyl bromide in 20 ml of ethanol was added thereto at room temprature with stirring. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1 N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4.37 g of diethyl 2-acetamido-2-hexadecylmalonate.

Workup

  1. temperaturethe mixture was refluxed for about 15 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-79e8e6b7446948a791ca4c725398dd2f
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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