Triethylamine → 2-(Cyclopropanecarbonyl-amino)-propionic acid ethyl ester

HRID 1158982

반응식

HRID 1158982 반응식
Cl.[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH2:7])[CH3:3].C(N(CC)CC)C.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:2]([O:4][C:5](=[O:9])[CH:6]([NH:7][C:20]([CH:17]1[CH2:19][CH2:18]1)=[O:21])[CH3:8])[CH3:3]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

생성물 1

HCID 586367092-(Cyclopropanecarbonyl-amino)-propionic acid ethyl ester수율 96.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of L-alanine ethyl ester hydrochloride (50 g, 325 mmol) in anhydrous dichloromethane (800 mL) added triethylamine (65.8 g, 650 mmol) and stirred at room temperature for 30 minutes. To the reaction mixture cyclopropanecarbonyl chloride (50.96 g, 0.487 mole) was slowly added and stirred at room temperature for overnight. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a mixture of ethyl acetate:hexane (1:1) as eluant to give 2-(cyclopropanecarbonyl-amino)-propionic acid ethyl ester (163) (58.0 g, 96% yield).

후처리

  1. stirringstirred at room temperature for overnight
  2. extractionthe crude product extracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a crude residue, which
  6. customwas purified by column chromatography on silica gel using
  7. additiona mixture of ethyl acetate:hexane (1:1) as eluant

출처 및 근거

ORD 기록
ord-69d17007803b427585abb2ed6ba25eae
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812037B2

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