L-Aspartic Acid → Ethylene Aspartate Cysteate

HRID 1378304

반응식

HRID 1378304 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[NH2:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][S:13](=[O:16])([OH:15])=[O:14].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28](Br)[CH2:29]Br>C(O)C.O>[NH2:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][S:13](=[O:15])([OH:16])=[O:14].[NH2:1][C@@H:2]1[C:7](=[O:9])[O:8][CH2:29][CH2:28][O:6][C:4](=[O:5])[CH2:3]1

참가 물질

8

반응물 5

HCID 5960L-Aspartic AcidHCID 78391,2-DibromoethaneHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 72886L-Cysteic acid

생성물 1

HCID 86751243Ethylene Aspartate Cysteate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A 500 ml three necked round bottom flask equipped with a mechanical stirrer, thermometer and reflux condenser was charged with 3.54 g (0.0266 mol) L-aspartic acid, 14.94 g (0.0798 mol) L-cysteic acid and 133 ml water. Add 8.51 g (0.2128 mol) sodium hydroxide and 5.64 g (0.0532 mol) sodium carbonate with moderate stirring. The reaction mixture exotherms to about 40° C. After all has dissolved, add 80 ml ethanol and 12.5 g (0.0665 mol) ethylene dibromide. Heat the reaction mixture to reflux (~84° C.) for 24 hours. Replace the reflux condenser with a short path distillation head and distill off the ethanol and excess ethylene dibromide. Place the flask in a water bath, heat to 70° C. and remove trace amounts of ethylene dibromide under high vacuum. The crude yield of the reaction mixture was 34.6 g. This mixture was determined to contain salt, L-aspartic acid disodium salt, L-cysteic acid disodium salt, Na4EDC, Na4EDDS and Na4EAC. The purity of this product was found to be about 50-70% sequestrant by C13 nuclear magnetic resonance analysis.

후처리

  1. temperaturethermometer and reflux condenser
  2. customexotherms to about 40° C
  3. dissolutionAfter all has dissolved
  4. temperatureHeat the reaction mixture
  5. temperatureto reflux (~84° C.) for 24 hours
  6. distillationReplace the reflux condenser with a short path distillation head
  7. distillationdistill off the ethanol and excess ethylene dibromide
  8. customremove trace amounts of ethylene dibromide under high vacuum

출처 및 근거

ORD 기록
ord-a2c920ce71fc40ad85451b25eb750443
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668098

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