Hydroxide → 7-demethylmitomycin A

HRID 1682136

反応式

HRID 1682136 の反応式
[OH-:1].[Na+].[OH-].[CH3:4][C:5]1[C:11](=[O:12])[C:10]2[N:13]3[C@@:17]([O:24][CH3:25])([C@H:18]([CH2:19][O:20][C:21]([NH2:23])=[O:22])[C:9]=2[C:7](=[O:8])[C:6]=1N)[C@H:16]1[NH:26][C@H:15]1[CH2:14]3.[H][H]>CO>[CH3:4][C:5]1[C:6](=[O:1])[C:7](=[O:8])[C:9]2[C@@H:18]([CH2:19][O:20][C:21]([NH2:23])=[O:22])[C@@:17]3([O:24][CH3:25])[C@H:16]4[NH:26][C@H:15]4[CH2:14][N:13]3[C:10]=2[C:11]=1[OH:12]

参加物

6

反応物 4

HCID 961HydroxideHCID 5746Mitomycin CHCID 14798Sodium HydroxideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 117273937-demethylmitomycin A

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Turning now to preferred conditions for the wet route, the aqueous solution of 7-salt oxide-9a-methoxymitosane (7-Na+O- -9a-methoxymitosane when aqueous sodium hydroxide is the hydroxide solution reacted with mitomycin C) is reacted directly with acid. While aqueous acid solutions or strong acid cation exchange resin in the hydrogen form can be used as the acidifying agent, in this case, unlike in the dry route, aqueous acid solution is preferred over cation exchange resin since use of cation exchange resin requires a resin separation step whereas the water introduced with aqueous acid does not need to be removed for reaction of diazodiphenylmethane with 7-hydroxy-9a-methoxymitosane. The reaction is readily carried out, for example, by combining diphenyldiazomethane solution with the 7-salt oxide-9a-methoxymitosane solution, adjusting the pH into the desired range of about 4 to 7 with acid solution, preferably 5-15% phosphoric acid, maintaining the pH in said desired range by the periodic addition of acid solution while maintaining the temperature in the range of 0° C. to 30° C. and adding additional diphenyldiazomethane solution if needed. As previously indicated methanol is preferably used in combination with methylene chloride reaction solvent. The methanol aids in extracting formed 7-hydroxy-9a-methoxymitosane from aqueous phase for reaction in the organic phase with diazodiphenylmethane.

後処理

  1. customis reacted directly with acid
  2. customa resin separation step whereas the water
  3. additionintroduced with aqueous acid
  4. customto be removed for reaction of diazodiphenylmethane with 7-hydroxy-9a-methoxymitosane
  5. temperaturemaintaining the pH
  6. additionby the periodic addition of acid solution
  7. temperaturewhile maintaining the temperature in the range of 0° C. to 30° C.
  8. additionadding additional diphenyldiazomethane solution
  9. customAs previously indicated methanol is preferably used in combination with methylene chloride reaction solvent
  10. extractionin extracting

出典と根拠

ORDレコード
ord-69ef66cecedf4868a80aa55af9583baa
出典データセット
uspto-grants-1992_12
特許番号
US05175303

関連ノート

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