Dicyclohexylcarbodiimide → N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide

HRID 745625노트

반응식

HRID 745625 반응식
[CH2:1]([O:3][C:4]([CH:6]([CH3:15])[CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=O)=[O:5])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:31][NH:32][C:33](=[O:45])[C@H:34]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[NH2:35].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:31][NH:32][C:33](=[O:45])[C@H:34]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=1)[NH:35][C:8](=[O:10])[CH:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:15]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 14303038O-methyl-L-tyrosine N-MethylamideHCID 199634113-(Ethoxycarbonyl)-2-(2-methylpropyl)butanoic acid

생성물 1

HCID 54114084N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

A mixture of 3-(ethoxycarbonyl)-2-(2-methylpropyl)butanoic acid (7.5 g., 0.037 mol.) and dichloromethane (70 mls.) was stirred and cooled to 0° C. To the mixture was added dropwise a solution of N,N'-dicyclohexylcarbodiimide (7.6 g., 0.37 mol.) in dichloromethane (20 mls.) and the reaction mixture was allowed to warm to room temperature. A solution of O-methyl-L-tyrosine N-methylamide (7.7 g., 0.037 mol.) in dichloromethane (45 mls.) was added to the reaction mixture and the resulting mixture was stirred overnight at room temperature. A saturated sodium bicarbonate solution (100 mls.) was added to the reaction mixture and the resulting mixture was stirred for an additional hour. The reaction mixture was filtered and the organic layer recovered and then dried on anhydrous sodium sulfate. The solvent was removed by evaporation in vacuo to yield a sticky brown solid. The solid was purified by chromatography on normal phase silica eluting with 20% hexane in ethyl acetate to yield N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)butanoyl]-O-methyl-L-tyrosine N-methylamide as a mixture of 4 diastereomers.

후처리

  1. temperatureto warm to room temperature
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. stirringthe resulting mixture was stirred for an additional hour
  4. filtrationThe reaction mixture was filtered
  5. customthe organic layer recovered
  6. dry with materialdried on anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation in vacuo
  8. customto yield a sticky brown solid
  9. customThe solid was purified by chromatography on normal phase silica eluting with 20% hexane in ethyl acetate

출처 및 근거

ORD 기록
ord-c1ebe605629b4d7e9ce890b6439fe495
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599361

반응 노트

불러오는 중…