Sodium Hypochlorite → N-(ortho-toluyl) dehydroalanine

HRID 362751노트

반응식

HRID 362751 반응식
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9]C(O)=O.Cl[O-].[Na+]>CO>[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:13]([OH:15])=[O:14])=[CH2:9]

참가 물질

4

반응물 2

HCID 23665760Sodium HypochloriteHCID 53943364N-(ortho-toluyl)aspartic acid

생성물 1

HCID 67584217N-(ortho-toluyl) dehydroalanine수율 33.4%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

10 g of N-(ortho-toluyl)aspartic acid are disolved in 20 ml of methanol in a 500 ml, three-necked, round-bottomed flask equipped with a thermometer, a dropping funnel and a reflux condenser. After having completely dissolved, 28.5 ml of an aqueous sodium hypochlorite solution, assaying at 1.40 mol/l, are added dropwise while maintaining the temperature below 20 °C. At the end of the addition, the mixture is diluted with 180 ml of methanol before being brought to reflux for 1 h 30 minutes. After concentrating under vacuum, the residue is taken up in ethyl acetate and extracted with an aqueous sodium bicarbonate solution. The aqeuous phase is acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with brine before being dried and concentrated under vacuum to provide an oil which crystallizes on addition of water. The precipitate formed is filtered and purified by recrystallization from water (a few drops of methanol are added, if necessary) to provide 2.65 g of N-(ortho-toluyl) dehydroalanine. (Nonoptimized yield 32%).

후처리

  1. customthree-necked, round-bottomed flask equipped with a thermometer, a dropping funnel and a reflux condenser
  2. dissolutionAfter having completely dissolved
  3. additionare added dropwise
  4. temperaturewhile maintaining the temperature below 20 °C
  5. additionAt the end of the addition
  6. temperatureto reflux for 1 h 30 minutes
  7. concentrationAfter concentrating under vacuum
  8. extractionextracted with an aqueous sodium bicarbonate solution
  9. extractionextracted with ethyl acetate
  10. washThe organic phase is washed with brine
  11. custombefore being dried
  12. concentrationconcentrated under vacuum
  13. customto provide an oil which
  14. customcrystallizes on addition of water
  15. customThe precipitate formed
  16. filtrationis filtered
  17. custompurified by recrystallization from water (a few drops of methanol are added, if necessary)

출처 및 근거

ORD 기록
ord-fdfa7305ebe640e0aeed2bd069000caf
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05871755

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