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

HRID 471689Notes

Reaction equation

HRID 471689 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-93d66082b7a0476c9cda3b59b72e693e
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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