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Tris(hydroxymethyl)aminomethane → Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}phenoxy)methyl]-benzoate

HRID 899899
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899899
[CH2:1]([N:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].Br[CH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].C(O)C(N)(CO)CO>C(#N)C>[CH2:1]([N:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:10][CH:11]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 69120480N-ethyl-N-(2-fluorobenzyl)-2-(4-hydroxyphenyl)acetamide

Produkt 1

HCID 69120251Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}phenoxy)methyl]-benzoateAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

N-Ethyl-N-(2-fluorobenzyl)-2-(4-hydroxyphenyl)acetamide (0.381 g, 1.327 mmol) and methyl 2-(bromomethyl)benzoate (0.334 g, 1.460 mmol) were dissolved in acetonitrile (10 ml) and potassium carbonate (0.367 g, 2.654 mmol) was added. The mixture was stirred at 65° C. for three hours. When N-ethyl-N-(2-fluorobenzyl)-2-(4-hydroxyphenyl)acetamide was consumed, PS-trisamine (0.3 eqv) was added and the solution was stirred overnight at room temperature. The polymer was filtered off and acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of water, dried (MgSO4) and the solvent was removed by evaporation to give 0.545 g of methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (yield 94.3%).

Aufarbeitung

  1. customWhen N-ethyl-N-(2-fluorobenzyl)-2-(4-hydroxyphenyl)acetamide was consumed
  2. stirringthe solution was stirred overnight at room temperature
  3. filtrationThe polymer was filtered off
  4. customacetonitrile was removed by evaporation
  5. additionEtOAc (10 ml) was added
  6. washthe organic phase was washed with two portions of water
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-33f09f29f70b4438a78ffa9b6631477e
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07355069B2

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