Hydrochloric Acid → 5-{{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-carboxycyclopropyl) methyl]amino}-2-fluorobenzoic acid

HRID 551969

Reaktionsgleichung

Reaktionsgleichung von HRID 551969
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:30][CH:31]3[CH2:33][CH:32]3[C:34]([O:36]CC)=[O:35])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26]C)=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+].O.Cl>C1COCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:30][CH:31]3[CH2:33][CH:32]3[C:34]([OH:36])=[O:35])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554524Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoate

Produkt 1

HCID 116217505-{{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-carboxycyclopropyl) methyl]amino}-2-fluorobenzoic acidAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}{[2-(ethoxycarbonyl)cyclopropyl]methyl}amino)-2-fluorobenzoate (340 mg; 0.63 mmol) in anhydrous THF (5 mL) were added lithium hydroxide monohydrate (64 mg; 1.54 mmol) and water (7 mL). The reaction mixture was stirred under MW at 100° C. for 2500 s. Then an aqueous solution of HCl (1N) was added, the residue was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (60 mL), dried over magnesium sulfate and the solvent was removed under reduced pressure to give 230 mg (73%) of the title compound as a white solid. HPLC, Rt: 4.99 min (purity 99.5%). LC/MS: M−(ESI): 498.2, 1H NMR (MeOD) δ: 7.46 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.3 Hz, 2H), 7.29 (m, 3H), 7.21 (d, J=7.9 Hz, 2H), 4.66 (s, 2H), 3.44 (m, 1H), 2.65 (t, J=7.5 Hz, 2H), 1.65 (m, 3H), 1.35 (m, 3H), 1.15 (m, 1H), 0.95 (m, 4H), 3.59 (m, 1H), 7.05 (m, 2H).

Aufarbeitung

  1. extractionthe residue was extracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with brine (60 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-03dfc9bda7f34860b68813fecd5bc4a3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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