Pipecolic Acid → Pipecolic acid, (-)-

HRID 845724

반응식

HRID 845724 반응식
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].C(O)(=O)[C@H]([C@@H](C(O)=O)O)O>CO>[CH2:7]1[CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH:1][CH2:9][CH2:8]1

참가 물질

4

반응물 2

HCID 849Pipecolic AcidHCID 439655D-Tartaric acid

생성물 1

HCID 439227Pipecolic acid, (-)-

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

483 g (=3.75M) of enriched (-)-pipecolic acid are suspended in 3 liters of hot methanol. 565 g of D-(-)-tartaric acid are rapidly scattered in and an attempt made as quickly as possible to obtain a solution. Crystallization commences before a complete dissolution can be achieved. The mixture is cooled, filtered and well washed with methanol. The filtrate is concentrated and recrystallized. The obtained crystals are dissolved hot in ca 800 ml of water and 400 ml at acetone and treated with active charcoal. The clear almost colorless filtrate is diluted with ca 2 liters of acetone. The resulting crystals are filtered of and well washed with acetone/H2O 4:1 followed by 100% acetone. The filtrate is concentrated and diluted with acetone to obtain a second fraction. Both fractions are dried. [α]D20 =20.3° for the first fraction and -20.7° for the second fraction, (c=2, H2O) total weight 706 g. Separation is effected with 3 liters of Amberlite 7R 120 in the H+ form. After working the tartrate salt with 10% ammonia, the L-(-)-pipecolic acid is obtained by elution and concentration by evaporation and then once recrystalized out of a minimum of H2O and a maximum of alcohol, [α]D20 -27.5 (C=2, H2O).

후처리

  1. customto obtain a solution
  2. customCrystallization commences
  3. dissolutionbefore a complete dissolution
  4. temperatureThe mixture is cooled
  5. filtrationfiltered
  6. washwell washed with methanol
  7. concentrationThe filtrate is concentrated
  8. customrecrystallized
  9. dissolutionThe obtained crystals are dissolved hot in ca 800 ml of water
  10. addition400 ml at acetone and treated with active charcoal
  11. additionThe clear almost colorless filtrate is diluted with ca 2 liters of acetone
  12. filtrationThe resulting crystals are filtered of and
  13. washwell washed with acetone/H2O 4:1
  14. concentrationThe filtrate is concentrated
  15. additiondiluted with acetone
  16. customto obtain a second fraction
  17. customBoth fractions are dried
  18. custom[α]D20 =20.3°
  19. customfor the first fraction and -20.7°
  20. customSeparation

출처 및 근거

ORD 기록
ord-394a2e42f5ac46cd91d618506daefeab
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04760065

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