Diisopropylethylamine → HCID 69259345, compound

HRID 898919Notes

Reaction equation

HRID 898919 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([CH2:9][NH:10][CH2:11][CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.Cl[C:25](=[O:47])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36][C:37]2[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=2[C:39]([O:41][CH3:42])=[O:40])=[CH:30][CH:29]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:11][CH3:12])[C:25](=[O:47])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36][C:37]3[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=3[C:39]([O:41][CH3:42])=[O:40])=[CH:30][CH:29]=2)=[CH:13][CH:14]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13798684HCID 13798684, compoundHCID 86600967Benzoic acid, 2-[2-[4-(2-chloro-2-oxoethoxy)phenyl]ethoxy]-, methyl ester

Product 1

HCID 69259345HCID 69259345, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(4-tert-butylbenzyl)-N-ethylamine (0.143 g, 0.746 mmol) was dissolved in dry acetonitrile under N2 and N-ethyl-N,N-diisopropylamine (0.371 g, 2.867 mmol) was added. The mixture was stirred for 30 min and methyl 2-{2-[4-(2-chloro-2-oxoethoxy)phenyl]ethoxy}benzoate (0.200 g, 0.573 mmol) was added. The solution was stirred overnight at room temperature. The crude was purified by flash cromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 0.229 g of methyl 2-[2-(4-{2-[(4-tert-butylbenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate (yield 79.3%).

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. customThe crude was purified by flash cromatography (
  3. concentrationthe EtOAc concentration
  4. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
  5. additionThe product containing fractions
  6. customthe EtOAc was removed by evaporation

Sources & evidence

ORD record
ord-7e69d953d341476aab089c52556eeac8
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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