Sodium Carbonate → ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoate

HRID 1587337Notes

Reaction equation

HRID 1587337 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][NH:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:5])[CH3:2].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:1]([O:3][C:4]([CH2:6][N:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 281012Ethyl 3-(ethoxycarbonylmethylamino)propionate

Product 1

HCID 4381617ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 49 g of ethyl N-(ethoxycarbonylmethyl)-β-alaninate and 30 ml of water cooled to -10° is added dropwise 27.6 ml of ethyl chloroformate followed by a solution of 12.7 g of sodium carbonate in 50 ml of water. The mixture is warmed to room temperature then heated at 55° for 50 minutes. The mixture is cooled, extracted with toluene, the extract is washed with 2N hydrochloric acid and water. The extract is dried over sodium sulfate, filtered, concentrated and distilled in vacuo to yield ethyl N-(ethoxycarbonylmethyl)-N-(ethoxycarbonyl)-β-alaninate.

Workup

  1. temperaturecooled to -10°
  2. temperaturethen heated at 55° for 50 minutes
  3. temperatureThe mixture is cooled
  4. extractionextracted with toluene
  5. washthe extract is washed with 2N hydrochloric acid and water
  6. dry with materialThe extract is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-b02302568f964419b62ac05ffbc53f1b
Source dataset
uspto-grants-1993_06
Patent number
US05217963

Reaction notes

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