Acetamidomalonic acid diethyl ester → HCID 53699606, compound

HRID 1382238Notes

Reaction equation

HRID 1382238 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:11][C:12](=[O:14])[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[O-]CC.[Na+].Br[CH:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:22]>C(O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]([NH:11][C:12](=[O:14])[CH3:13])([CH:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH3:10]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 111723781-(1-bromoethyl)naphthalene

Product 1

HCID 53699606HCID 53699606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetylaminopropanedioic acid diethyl ester (20.8 g) was added to a solution of sodium ethoxide in ethanol (prepared from sodium (2.2 g) and ethanol (100 ml)). After the mixture was stirred for 10 minutes at ambient temperature, 1-(1-bromoethyl)naphthalene was added. The reaction mixture was stirred for 18 hours at room temperature. The precipitated solid was collected by filtration and dissolved in chloroform. The chloroform solution was dried over magnesium sulfate and evaporated to give 2-acetylamino-2-[1-(1-naphthyl)ethyl]propanedioic acid diethyl ester (21.59 g).

Workup

  1. stirringThe reaction mixture was stirred for 18 hours at room temperature
  2. filtrationThe precipitated solid was collected by filtration
  3. dissolutiondissolved in chloroform
  4. dry with materialThe chloroform solution was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-79cf844dd51a4c25a191e14da9927989
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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