1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-(benzyloxy)ethyl)-3-hydroxy-2,2-dimethylpropanamide

HRID 471689ノート

反応式

HRID 471689 の反応式
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=O.[CH2:9]([O:16][CH2:17][CH2:18][NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>ClCCl>[CH2:9]([O:16][CH2:17][CH2:18][NH:19][C:4](=[O:6])[C:3]([CH3:8])([CH3:7])[CH2:2][OH:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 5338682-(Benzyloxy)ethanamine

生成物 1

HCID 66745964N-(2-(benzyloxy)ethyl)-3-hydroxy-2,2-dimethylpropanamide収率 97.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-hydroxy-2,2-dimethylpropanoic acid (2.36 g, 20 mmol), 2-(benzyloxy)ethanamine (3.02 g, 20 mmol), and HOBt (2.71 g, 20 mmol) in dry dichloromethane (100 mL) was added EDCI (3.82 g, 20 mmol) at room temperature under nitrogen. The reaction mixture was then stirred at room temperature under nitrogen overnight. The reaction was quenched with brine, and extracted with EtOAc (3×). The combined organic layers were washed with saturated NaHCO3 solution, dilute HCl, brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 40% EtOAc in hexanes to give the title compound as colorless oil (4.89 g) in 97% yield. MS 252 (MH+).

後処理

  1. customThe reaction was quenched with brine
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with saturated NaHCO3 solution, dilute HCl, brine
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by chromatography on silica gel eluting with 40% EtOAc in hexanes

出典と根拠

ORDレコード
ord-93d66082b7a0476c9cda3b59b72e693e
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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