Sodium Hydroxide → 4-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluoro-benzoic acid
Reaktionsgleichung
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[C:7]([Cl:25])[C:6]=1[NH:26][CH:27]1[CH2:29][CH2:28]1)C.[OH-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[C:21]([O:20][C:18]([NH:17][C@H:14]1[CH2:15][CH2:16][N:12]([C:8]2[C:9]([F:11])=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([NH:26][CH:27]3[CH2:28][CH2:29]3)[C:7]=2[Cl:25])[CH2:13]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3c, 2.90 g, 6.56 mmol) in methanol (30 mL) and tetrahydrofuran (30 mL) is added a 1N solution of sodium hydroxide (50 mL). The reaction mixture is stirred at 80° C. for 20 hours, cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with 1N hydrochloric acid, water, and brine. The organic layer is dried over MgSO4, filtered, and filtrate concentrated to the title compound as a solid (2.74 g). MS CI: m/z 414 (MH+).
Aufarbeitung
- temperaturecooled to room temperature
- washThe organic layer is washed with 1N hydrochloric acid, water, and brine
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- concentrationfiltrate concentrated to the title compound as a solid (2.74 g)
Quellen und Nachweise
- ORD-Eintrag
- ord-f50aebfc14dc4b5b841a5c5a8c95fbd6
- Quelldatensatz
- uspto-grants-2009_09
- Patentnummer
- US07582627B2
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