Diethyl Ether → HCID 13560381, compound

HRID 1284641Notes

Reaction equation

HRID 1284641 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH3:3].C([CH:13]([C:17](Cl)=[O:18])[C:14](Cl)=[O:15])C.C(=O)([O-])[O-].[K+].[K+].[CH3:26][CH2:27][O:28]CC>O>[CH2:27]([O:28][C:17]([CH2:13][C:14]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:15])=[O:18])[CH3:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 109209242-Ethylpropanedioyl dichlorideHCID 13454968ethyl 2-(propylamino)acetate

Product 1

HCID 13560381HCID 13560381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.16 g (49.4 mM) of ethyl N-(n-propyl)glycinate and 6.4 ml (50 mM) of ethyl malonyl chloride were added simultaneously to an ice-cold solution of 6.9 g (50 mM) of potassium carbonate in 15 ml water overlaid with 50 ml ether. The cooling bath was removed and the reaction warmed to ambient temperature stirring for 1.5 hours. The aqueous phase was acidified to pH 4 with concentrated HCl and the layers separated. The aqueous phase was extracted with 15 ml ether and the combined ether layer washed with brine and dried over anhydrous Na2SO4 then concentrated to yield 11.8 g of the desired product as a pale yellow oil.

Workup

  1. customThe cooling bath was removed
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with 15 ml ether
  4. washthe combined ether layer washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationthen concentrated

Sources & evidence

ORD record
ord-c5310d36956e45afaf4a6588a196ca15
Source dataset
uspto-grants-1986_01
Patent number
US04563525

Reaction notes

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