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

HRID 745618노트

반응식

HRID 745618 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e11f443478c4171bd3e16b20457b0b1
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599361

반응 노트

불러오는 중…