Potassium Hydroxide → 2-[(4-{2-[Heptyl(2-phenylethyl)amino]-2-oxoethyl}-phenoxy)methyl]benzoic acid

HRID 2112051

Reaktionsgleichung

Reaktionsgleichung von HRID 2112051
[CH2:1]([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9](=[O:29])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[K+]>CCO>[CH2:1]([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9](=[O:29])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[CH:27][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 68869824Methyl 2-[(4-{2-[heptyl(2-phenylethyl)amino]-2-oxoethyl}phenoxy)methyl]-benzoate

Produkt 1

HCID 104581652-[(4-{2-[Heptyl(2-phenylethyl)amino]-2-oxoethyl}-phenoxy)methyl]benzoic acidAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl 2-[(4-{2-[heptyl(2-phenylethyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (0.146 g, 0.291 mmol) was dissolved in EtOH (5 ml, 95%), potassium hydroxide (0.025 g, 0.437 mmol) was added. The reaction was performed in an single node microwave oven (7 min, 150° C.). Work-up was by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The water-phase was extracted with two portions of EtOAc (20 ml) and the organic phase was dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with isocratic 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 were pooled and the acetonitrile was removed by evaporation EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). The solvent was removed by evaporation to give 0.043 g of 2-[(4-{2-[heptyl(2-phenylethyl)amino]-2-oxoethyl}-phenoxy)methyl]benzoic acid (yield 30.3%).

Aufarbeitung

  1. customThe reaction was performed in an single node microwave oven
  2. custom(7 min, 150° C.)
  3. customby removing the solvent
  4. customby evaporation and addition of HCl (2 ml, 1 M)
  5. extractionThe water-phase was extracted with two portions of EtOAc (20 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation
  8. customThe crude was purified by preparative HPLC (
  9. concentrationthe acetonitrile concentration
  10. temperaturewas increased to 100%
  11. 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)
  12. additionThe product containing fractions
  13. customthe acetonitrile was removed by evaporation EtOAc (10 ml)
  14. additionwas added
  15. washthe organic phase was washed with two portions of brine
  16. dry with materialdried (MgSO4)
  17. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-344ff2ade96445399e267108422d9551
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521461B2

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