Sodium hydride → 5-L-glutamyl-taurine

HRID 2285689ノート

反応式

HRID 2285689 の反応式
[Na+].C([NH:12][C@H:13]([C:19]([O-:21])=[O:20])[CH2:14][CH2:15][C:16](=[O:18])[NH2:17])(OCC1C=CC=CC=1)=O.[H-].[Na+].Br[CH:25]([S:27]([O-:30])(=[O:29])=[O:28])[CH3:26].[Na+]>CN(C)C=O>[NH2:12][C@H:13]([C:19]([OH:21])=[O:20])[CH2:14][CH2:15][C:16]([NH:17][CH2:26][CH2:25][S:27]([OH:30])(=[O:29])=[O:28])=[O:18]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 23705444Sodium bromoethanesulfonateHCID 70546861carbobenzyloxy-L-glutamine sodium salt

生成物 1

HCID 687595-L-glutamyl-taurine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3.02 g. (10 mmoles) of carbobenzyloxy-L-glutamine sodium salt (Liebig's Ann. 640, 145 /1961/) are dissolved in 50 ml. of dimethyl formamide, 12 mmoles of sodium hydride are added in the form of an oily dispersion, and the mixture is heated for 2 hours under exclusion of air humidity. Thereafter a solution of 2.11 g. (10 mmoles) of sodium bromoethanesulfonate in 50 ml. of dimethyl formamide is added dropwise, and the mixture is heated for additional 2 hours. The mixture is evaporated in vacuo. The residue is extracted with ether, then the dry substance is dissolved in water, and the solution is passed through a column filled with Dowex 50 ion exchanger. The column is eluted with water. The eluate is evaporated in vacuo, and the residue is dried over solid potassium hydroxide. The obtained substance is subjected to catalytic hydrogenation as described in Example 5. The product is recrystallized from a mixture of ethanol and water. 1.55 g. of gamma-L-glutamyl-taurine are obtained.

後処理

  1. temperaturethe mixture is heated for 2 hours under exclusion of air humidity
  2. temperaturethe mixture is heated for additional 2 hours
  3. customThe mixture is evaporated in vacuo
  4. extractionThe residue is extracted with ether
  5. dissolutionthe dry substance is dissolved in water
  6. additionfilled with Dowex 50 ion exchanger
  7. washThe column is eluted with water
  8. customThe eluate is evaporated in vacuo
  9. dry with materialthe residue is dried over solid potassium hydroxide
  10. customThe product is recrystallized from a mixture of ethanol and water

出典と根拠

ORDレコード
ord-da5cbcf82c7e412ea838dd7772afafaf
出典データセット
uspto-grants-1982_04
特許番号
US04324743

反応ノート

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