4-Methylmorpholine → N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide

HRID 1252378ノート

反応式

HRID 1252378 の反応式
[CH2:1]([O:3][C:4]([CH2:6][CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=O)=[O:5])[CH3:2].CN1CCOCC1.C(Cl)(=O)C(Cl)=O.[CH3:28][NH:29][C:30](=[O:42])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[NH2:32]>ClCCl.CN(C)C=O>[CH3:28][NH:29][C:30](=[O:42])[C@H:31]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)[NH:32][C:8](=[O:10])[CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 65578Oxalyl chlorideHCID 143030363-(Ethoxycarbonyl)-2-(2-methylpropyl)propanoic acidHCID 14303038O-methyl-L-tyrosine N-Methylamide

生成物 1

HCID 14303040N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

A mixture of 3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoic acid (17.4 g., 0.087 mol.), N-methylmorpholine (28.7 mls., 0.26 mol.) and dimethylformamide (0.25 ml.) was dissolved in dry dichloromethane (200 mls.) and the resulting mixture was cooled to 0° C. To the reaction mixture was added a solution of oxalyl chloride (7.6 mls., 0.087 mol.) in dry dichloromethane (50 mls.). The mixture was heated under reflux for 10 minutes and then cooled to -70° C. To the reaction mixture was added O-methyl-L-tyrosine N-methylamide (20.0 g, 0.096 mol.) in dry dichloromethane (100 mls.) over a period of 30 minutes. The resulting mixture was allowed to warm to room temperature and stirred for 2.5 days. The mixture was filtered and the filtrate washed with saturated sodium bicarbonate solution (2×200 mls.), dilute citric acid (2×150 mls.) and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation in vacuo to yield N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide, as a mixture of isomers (20.7 g.), in the form of a solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturecooled to -70° C
  4. temperatureto warm to room temperature
  5. filtrationThe mixture was filtered
  6. washthe filtrate washed with saturated sodium bicarbonate solution (2×200 mls.), dilute citric acid (2×150 mls.)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation in vacuo

出典と根拠

ORDレコード
ord-04ae1032c119411ba80baa02318a89cc
出典データセット
uspto-grants-1988_05
特許番号
US04743587

反応ノート

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