Hydrochloric Acid → (+/-)-4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid

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Reaktionsgleichung

C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH:24]2[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25]2)[NH:12][C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH3:28][C:26]1([CH3:29])[CH2:25][CH:24]([CH:11]([NH:12][C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=2)[CH2:27]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

(+/−)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid ethyl ester (Intermediate 25) (43 mg, 0.11 mmol) was dissolved in tetrahydrofuran (3 mL) and methanol (1 mL), and 1.0 M NaOH (2 mL) was added. This was stirred at 50° C. at first as a suspension then as a clear solution for 4 h before cooling to room temperature. 1 N HCl was added until the solution was pH 5. This was extracted twice with ethyl acetate and the combined organics were dried over MgSO4. The solution was concentrated in vacuo to give (+/−)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid (37.7 mg) as a white solid. MS (M+1): 375.1.

Aufarbeitung

temperatureas a clear solution for 4 h before cooling to room temperature
extractionThis was extracted twice with ethyl acetate
dry with materialthe combined organics were dried over MgSO4
concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-25b76d30cbfb4109b258b862266f0ca0
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09139538B2

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