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Sodium Hydroxide → 3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cycloh epten-5-yi]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid

HRID 394643
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Reaktionsgleichung

Reaktionsgleichung von HRID 394643
C([O:3][C:4](=[O:36])[CH:5]([O:33][CH2:34][CH3:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][CH2:21][C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]2=3)[CH3:17])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:29]1[C:20]2[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:18]([N:16]([CH3:17])[CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:33][CH2:34][CH3:35])[C:4]([OH:36])=[O:3])=[CH:12][CH:11]=3)[C:19]=2[CH:32]=[CH:31][CH:30]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 98700773-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester

Produkt 1

HCID 98688363-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cycloh epten-5-yi]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester (example 10)(1.5 g, 3.07 mmol) was dissolved in ethanol (20 ml) and 20% sodium hydroxide (2 ml) was added. After 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (2 ml) were added and the mixture was extracted with dichloromethane. The organic phase was dried (MgSO4) and the solvent evaporated in vacuo. The residue (1.4 g) was dissolved in acetone and neutralized with solution of hydrogen chloride in diethyl ether. The solvents were evaporated and the residue was triturated with diethyl ether yielding 1.15 g (74%) of the title compound as amorphous solid (hemihydrate). 1H NMR (250 MHz, DMSO-d6) δ10.50 (bs, 1 H); 7.60 (bs)+7.10-7.50 (m, 10 H), 6.87 (d, J=7.9 Hz, 2 H), 5.84 (bd, J=7.0 Hz, 1 H), 4.49 (bs, 2 H), 4.00 (t, J=5.6 Hz; +bm, 3 H), 3.30-3.60 (m+m, 4 H), 2.80-3.10 (s+bm, 7 H), 1.07 (t, J=7.2 Hz, 3 H).

Aufarbeitung

  1. customAfter 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (2 ml)
  2. additionwere added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe residue (1.4 g) was dissolved in acetone and neutralized with solution of hydrogen chloride in diethyl ether
  7. customThe solvents were evaporated
  8. customthe residue was triturated with diethyl ether yielding 1.15 g (74%) of the title compound as amorphous solid (hemihydrate)

Quellen und Nachweise

ORD-Eintrag
ord-20d2d48d4bd442eb87db450714e20d46
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06602901B2

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