1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(3,4-dichlorophenyl)-N-methoxy-N-methylpropanamide

HRID 1771096Notes

Reaction equation

HRID 1771096 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH3:15][NH:16][O:17][CH3:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([N:16]([O:17][CH3:18])[CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1411813-(3,4-Dichlorophenyl)propionic acid

Product 1

HCID 867281793-(3,4-dichlorophenyl)-N-methoxy-N-methylpropanamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4-dichlorophenyl)propanoic acid (0.50 g, 2.3 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.27 g, 2.7 mmol) in DCM (5 mL) was added EDCI (0.57 g, 3.0 mmol), HOBt (0.35 g, 2.3 mmol) and TEA (0.39 mL, 2.8 mmol). The reaction mixture was stirred at rt for 18 h, concentrated and the residue was purified by ISCO chromatography (EtOAc/Hexanes 0-100% over 20 min, column 40 g, flow rate 40 mL/min) to give Intermediate 15A (569 mg, 2.17 mmol, 95.0% yield) as a clear oil. HPLC/MS (Method R) RT=1.76 min, [M+1]+ 262.1.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by ISCO chromatography (EtOAc/Hexanes 0-100% over 20 min, column 40 g, flow rate 40 mL/min)

Sources & evidence

ORD record
ord-72ee01e4a175440981b2baa60c48da87
Source dataset
uspto-grants-2016_02
Patent number
US09249096B2

Reaction notes

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