Hydrochloric Acid → HCID 10743906, compound

HRID 1451568Notes

Reaction equation

HRID 1451568 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][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:39][CH2:38][CH2:37][CH2:36][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 14041Acetamidomalonic acid diethyl esterHCID 202711-BromoeicosaneHCID 2723922Sodium ethoxide

Product 1

HCID 10743906HCID 10743906, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. 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 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate.

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-5172c6ba62c648a98970c3edfd24e53e
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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