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3-(4-Hydroxyphenyl)propionic acid → N-butyl-N-(2,3-dimethoxybenzyl)-3-(4-hydroxyphenyl)propanamide

HRID 899882
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899882
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:4]=1[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](O)=[O:27])=[CH:20][CH:19]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[CH2:7]([N:6]([CH2:5][C:4]1[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:3]=1[O:2][CH3:1])[C:26](=[O:27])[CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([OH:17])=[CH:19][CH:20]=1)[CH2:8][CH2:9][CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4717318Butyl[(2,3-dimethoxyphenyl)methyl]amine

Produkt 1

HCID 69120686N-butyl-N-(2,3-dimethoxybenzyl)-3-(4-hydroxyphenyl)propanamideAusbeute 120,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(2,3-dimethoxybenzyl)butan-1-amine (0.59 g, 2.65 mmol) was dissolved in DMF (10 ml), 3-(4-hydroxyphenyl)propanoic acid (0.4 g, 2.41 mmol), was added and the mixture was cooled to 0° C. N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (0.85 g, 2.65 mmol) and diisopropylethylamine (0.65 g, 5.05 mmol) was added. The mixture was allowed to warm to room temperature and stirred over night. EtOAc (15 ml) was added and the organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml). EtOAc was removed by evaporation and the crude was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions was pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two potions of brine and dried (MgSO4). The solvent was removed by evaporation and gave 1.08 gram of N-butyl-N-(2,3-dimethoxybenzyl)-3-(4-hydroxyphenyl)propanamide (yield 82.3%).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washthe organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml)
  3. customEtOAc was removed by evaporation
  4. customthe crude was purified by preparative HPLC (
  5. concentrationthe acetonitrile concentration
  6. temperaturewas increased to 100%
  7. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  8. additionThe product containing fractions
  9. customthe acetonitrile was removed by evaporation
  10. additionEtOAc (10 ml) was added
  11. washthe organic phase was washed with two potions of brine
  12. dry with materialdried (MgSO4)
  13. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-73d1d648623d4041821e51cb503e5de9
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07355069B2

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