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

HRID 1467237Notes

Reaction equation

HRID 1467237 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-6fd75d21e31b4a0dbb3fecbac9cdd79e
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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