Sodium Chloride → Ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)-acetate

HRID 392894Notes

Reaction equation

HRID 392894 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:10][C:11]2[C:17]([CH3:18])=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=2[CH3:19])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:34](Cl)([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:35].C([O-])(O)=O.[Na+].[Na+].[Cl-]>ClCCl>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:10][C:11]2[C:12]([CH3:19])=[CH:13][C:14]([NH:15][C:34](=[O:35])[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:16][C:17]=2[CH3:18])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 516892Sodium BicarbonateHCID 155521874-[3-(4-Fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylaniline

Product 1

HCID 10114752Ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)-acetateYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

335 mg (0.96 mmol) of 4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylaniline (Example X) and 107 mg (1.06 mmol) of triethylamine are introduced into ml of dichloromethane and, at 0° C., 177 mg (1.29 mmol) of ethoxalyl chloride are added dropwise. The mixture is stirred for 4 h. It is shaken with NaHCO3 solution and NaCl solution, and the organic phase is dried and concentrated in a rotary evaporator. Purification by chromatography (cyclohexane/ethyl acetate=7:1) affords 231 mg of ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)-acetate.

Workup

  1. customthe organic phase is dried
  2. concentrationconcentrated in a rotary evaporator
  3. customPurification by chromatography (cyclohexane/ethyl acetate=7:1)

Sources & evidence

ORD record
ord-08c3f8ade2f04c15952a311000cc4c3e
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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