(+-)-Methionine → (-)-4'-Demethylepipodophyllotoxin

HRID 613776ノート

反応式

HRID 613776 の反応式
[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.NC(C(O)=O)CCSC.CS(O)(=O)=O.O>CC(C)=O>[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]

参加物

6

反応物 4

HCID 876(+-)-MethionineHCID 962WaterHCID 6395Methanesulfonic AcidHCID 10607Podophyllotoxin

生成物 1

HCID 122797(-)-4'-Demethylepipodophyllotoxin

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 50 g (0.12 mol) of podophyllotoxin I, prepared in 50 ml of acetone, is added with stirring at ordinary temperature to a mixture consisting of 100 g (0.67 mol) of D,L-methionine, of 500 ml (7.7 mol) of methanesulfonic acid and of 10 ml of water. The temperature rises to approximately 40° C. and stirring is maintained for 2 h with return to ambient temperature. The mixture is then poured onto ice in order to obtain a precipitate which is extracted with ethyl acetate (3×700 ml). The organic phases are washed with an NaHCO3 solution and then separated by settling, dried over Na2SO4, filtered and evaporated under reduced pressure in order to obtain 4'-demethylepipodophyllotoxin, existing in the form of a white solid. 45 g (Yd 94%) are obtained.

後処理

  1. additionis added
  2. customrises to approximately 40° C.
  3. stirringstirring
  4. additionThe mixture is then poured onto ice in order
  5. customto obtain a precipitate which
  6. extractionis extracted with ethyl acetate (3×700 ml)
  7. washThe organic phases are washed with an NaHCO3 solution
  8. customseparated
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated under reduced pressure in order

出典と根拠

ORDレコード
ord-2504db1eb8964f899c4a392884571edf
出典データセット
uspto-grants-1999_12
特許番号
US06008382

反応ノート

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