Glutaric Acid → HCID 178512808、化合物

HRID 746163ノート

反応式

HRID 746163 の反応式
N(CCCCCCC(NCl)=O)C(N)=N.Cl.Cl.NCCCNCCCCNC(=O)C(O)O.C(O)(=O)CCCC(O)=O.Cl.Cl.Cl.[NH2:44][CH2:45][CH2:46][CH2:47][NH:48][CH2:49][CH2:50][CH2:51][CH2:52][NH:53][C:54](=[O:70])[CH:55]([NH:57][C:58](=[O:69])[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][NH:65][C:66]([NH2:68])=[NH:67])[OH:56]>O>[NH2:44][CH2:45][CH2:46][CH2:47][NH:48][CH2:49][CH2:50][CH2:51][CH2:52][NH:53][C:54](=[O:70])[CH:55]([NH:57][C:58](=[O:69])[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][NH:65][C:66]([NH2:68])=[NH:67])[OH:56]

参加物

6

反応物 4

HCID 743Glutaric AcidHCID 133564GlyoxylylspermidineHCID 178478610HCID 178478610、化合物HCID 178512805HCID 178512805、化合物

生成物 1

HCID 178512808HCID 178512808、化合物収率 39%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
60 °C

実験手順

A mixture of 360 mg (1.62 mmoles) of 7-guanidinoheptanamido hydrochloride, 568 mg (1.94 mmoles) of N-[4-(3-aminopropyl)aminobutyl]-2,2-dihydroxyethanamide dihydrochloride obtained in Example 4, 214 mg (1.62 mmoles) of glutaric acid, and 0.36 ml of water was heated at 60° C. for 24 hours. After completion of the reaction, 5 ml of water was added to to the reaction mixture, then passed through a column (20 mm inner diameter) packed with 150 ml of CM-Sephadex® C-25 (Na-type), and fractionated by the gradient elution with 1.5 liters of water and 1.5 liters of 0.8M aqueous sodium chloride solution. The fractions containing the desired product were combined, then concentrated, and extracted three times with 10 ml of methanol. The methanol layer was passed through a column packed with 150 ml of Sephadex® LH-20, and developed with methanol. The fractions containing the desired product were combined and evaporated to dryness, yielding 317 mg (39% yield) of white powder of N-[4-(3-aminopropyl)aminobutyl]-2-(7-guanidinoheptanamido)-2-hydroxyethanamide trihydrochloride.

後処理

  1. additionwas added to to the reaction mixture
  2. wash(Na-type), and fractionated by the gradient elution with 1.5 liters of water and 1.5 liters of 0.8M aqueous sodium chloride solution
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated
  5. extractionextracted three times with 10 ml of methanol
  6. additionThe fractions containing the desired product
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-55d348351e954a7ba12c2c657f9ddc07
出典データセット
uspto-grants-1986_07
特許番号
US04603015

反応ノート

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