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

HRID 1158982

反応式

HRID 1158982 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-69d17007803b427585abb2ed6ba25eae
出典データセット
uspto-grants-2010_10
特許番号
US07812037B2

関連ノート

読み込み中…