Hydrochloric Acid → (-)-4'-Demethylepipodophyllotoxin

HRID 613775노트

반응식

HRID 613775 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9]C.Cl>C(Cl)Cl.C(OCC)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[OH:9]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 10607Podophyllotoxin

생성물 1

HCID 122797(-)-4'-Demethylepipodophyllotoxin

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

1 g of podophyllotoxin I is dissolved in a mixture of 15 ml of CH2Cl2 and 5 ml of ethyl ether. A slight stream of gaseous hydrochloric acid is introduced into the solution for 15 min at -10° C. and then stirring is maintained at this temperature for 1 h. After evaporating the reaction mixture without heating, 0.54 g of D,L-methionine and then 5 ml of methanesulfonic acid are added. After dissolving and stirring for 1 h with return to ordinary temperature, the reaction mixture is plunged into a water-acetone mixture and then BaCO3 is added to neutrality. After extracting with ethyl acetate, separating by settling, drying over Na2SO4, filtering and evaporating under reduced pressure, a residue is obtained which is crystallized from ethyl ether to provide 0.5 g (Yd 52%) of white crystals of 4'-demethylepipodophyllotoxin exhibiting a homogeneous spot by TLC.

후처리

  1. temperatureis maintained at this temperature for 1 h
  2. customAfter evaporating the reaction mixture
  3. temperaturewithout heating
  4. addition0.54 g of D,L-methionine and then 5 ml of methanesulfonic acid are added
  5. dissolutionAfter dissolving
  6. stirringstirring for 1 h with return to ordinary temperature
  7. additionBaCO3 is added to neutrality
  8. extractionAfter extracting with ethyl acetate
  9. customseparating
  10. dry with materialdrying over Na2SO4
  11. filtrationfiltering
  12. customevaporating under reduced pressure
  13. customa residue is obtained which
  14. customis crystallized from ethyl ether

출처 및 근거

ORD 기록
ord-d4caf1967a024645a3c2eda5724790e0
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008382

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