Methyl iodide → Methyl (S)-3-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoate
Reaktionsgleichung
IC.[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([O:15][CH3:23])=[O:14])=[O:9])([CH3:6])([CH3:4])[CH3:5]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Iodomethane (1.038 mL, 16.68 mmol) was added in one portion to (S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (1 g, 3.34 mmol) and potassium carbonate (0.922 g, 6.67 mmol) in DMF (15 mL). The resulting suspension was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and diluted with EtOAc (50 mL) with water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford (S)-methyl 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate (1.340 g, 128%) as a orange solid. 1H NMR (399.9 MHz, DMSO-d6) δ 1.36 (9H, s), 2.71-2.74 (1H, m), 2.74-2.80 (1H, m), 3.57 (3H, s), 4.91 (1H, d), 7.33 (2H, d), 7.39 (2H, d), 7.49 (1H, d). m/z (ESI−) (M−H)−=312; HPLC tR=2.57 min.
Aufarbeitung
- concentrationThe reaction mixture was concentrated
- additiondiluted with EtOAc (50 mL) with water (50 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-ddac0aa4e2424b8cbdcf299b8b53b0d5
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08101623B2
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