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Hydrochloric Acid → (4-{2-[5-(4-Cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

HRID 9690
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 9690
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[S:11][C:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]45OCC(C)(C[O:31]4)C[O:27]5)=[C:20]([CH3:35])[CH:19]=3)=[C:13]([CH3:15])[CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl>CC(O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]2[S:11][C:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:31])=[O:27])=[C:20]([CH3:35])[CH:19]=3)=[C:13]([CH3:15])[CH:14]=2)=[CH:9][C:2]=1[F:1])#[N:5]
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 219863002-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile2×

Produkt 1

HCID 21986517(4-{2-[5-(4-Cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile (intermediate 101, 0.016 g) in 2-propanol (2 ml) was treated with 2M aqueous hydrochloric acid (1 ml) and the mixture stirred at reflux for 2 hours. The solvent was removed and the residue dissolved in 1,4-dioxane (2 ml) and water (1 ml). This mixture was treated with 2M aqueous sodium hydroxide (0.5 ml) and the mixture stirred for 16 hours). The solvent was removed and the residue purified by SPE (aminopropyl). The title compound, as the free acid, was recovered by treating a solution of this product with Dowex H+.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in 1,4-dioxane (2 ml)
  4. additionThis mixture was treated with 2M aqueous sodium hydroxide (0.5 ml)
  5. stirringthe mixture stirred for 16 hours)
  6. customThe solvent was removed
  7. customthe residue purified by SPE (aminopropyl)
  8. customThe title compound, as the free acid, was recovered
  9. additionby treating a solution of this product with Dowex H+

Quellen und Nachweise

ORD-Eintrag
ord-8b8bdbd070704040b63b19183de9bb48
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091237B2

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