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

HRID 1252384노트

반응식

HRID 1252384 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

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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 over anhydrous sodium sulfate. The solvent was removed by evaporation in vacuo to yield a sticky brown solid. Th 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 over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation in vacuo
  8. customto yield a sticky brown solid
  9. customTh solid was purified by chromatography on normal phase silica eluting with 20% hexane in ethyl acetate

출처 및 근거

ORD 기록
ord-a8249f9fab5a45b594113ab24924a4ef
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743587

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