聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide

HRID 769

反应方程式

HRID 769 反应方程式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:32](O)=[O:33])[C@@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:16])[OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([C@H:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36].O.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:35]([C@H:37]([NH:44][C:32](=[O:33])[C@@H:27]([C@@H:28]([CH2:30][CH3:31])[CH3:29])[NH:26][C:24](=[O:25])[C@H:12]([CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:36]

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 757711-羟基苯并三唑(HOBT)HCID 6993773(S)-(-)-1-苯丙胺HCID 54543031N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine

产物 1

HCID 53679369N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide收率 33.1%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

To a solution of 6.69 g (14.2 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine and 2.04 g (15.1 mmols) of (S)-α-ethylbenzylamine in 200 ml of methylene chloride were added 2.73 g (14.2 mmols) of water-soluble carbodiimide hydrochloride and 1.92 g (14.2 mmols) of HOBt under cooling and stirred for one hour under cooling and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate was added. The resulting residue was washed two times each with 70 ml of aqueous 5% citric acid, once with 70 ml of water, two times each with 70 ml of aqueous 5% sodium hydrogencarbonate and once with 70 ml of brine in that order. The resulting organic layer was dried with anhydrous magnesium sulfate, the magnesium sulfate was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and concentrated under reduced pressure. The resulting solid residue was washed with ethyl acetate and dried to obtain 2.81 g (4.7 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide.

后处理

  1. temperatureunder cooling
  2. temperatureunder cooling
  3. customovernight
  4. customat room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate
  6. additionwas added
  7. washThe resulting residue was washed two times each with 70 ml of aqueous 5% citric acid
  8. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  9. customthe magnesium sulfate was removed by filtration
  10. concentrationthe resulting filtrate was concentrated under reduced pressure
  11. dissolutionThe resulting residue was dissolved in chloroform
  12. concentrationconcentrated under reduced pressure
  13. washThe resulting solid residue was washed with ethyl acetate
  14. customdried

来源与证据

ORD记录
ord-a473542e2c91474d920bd8a0505e632c
来源数据集
uspto-grants-1998_03
专利号
US05723165

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