Tetrahydrofuran → (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea
Reaktionsgleichung
C1C([N+]([O-])=O)=CC=C([Cl-][C:11]([O-:13])=O)C=1.Cl.[Cl:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].C[CH2:26][N:27](C(C)C)C(C)C.Cl.[CH3:35]N[C@@H](CC=C)CO.[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>>[Cl:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:11](=[O:13])[N:27]([C@@H:43]([CH2:44][CH:45]=[CH2:35])[CH2:47][OH:46])[CH3:26]Komponenten
5
Versuchsvorschrift
To a solution of 4-nitrophenylchloroformate 8 (2.28 g, 11.3 mmol) in THF (10 mL) was added a solution of 2-chloro-3-fluorobenzylamine hydrochloride (2.22 g, 11.3 mmol) and DIEA (5.38 mL, 30.9 mmol) in THF (10 mL). The resulting solution was stirred at RT for 20 min. The reaction solution was added into a solution of (S)-2-(methylamino)pent-4-en-1-ol hydrochloride (10.3 mmol), DIEA (5.38 mL, 30.9 mmol) in THF (100 mL). The resulting solution was stirred at RT for 1 h. The solvent was removed, and the resulting residue was purified on silica gel column using a mixture of DCM and MeOH to give (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea (2.56 g, 82%) as a white solid. LRMS (M+H+) m/z 301.2.
Aufarbeitung
- stirringThe resulting solution was stirred at RT for 1 h
- customThe solvent was removed
- customthe resulting residue was purified on silica gel column
- additiona mixture of DCM and MeOH
Quellen und Nachweise
- ORD-Eintrag
- ord-4691645a967d42bd880dbc1f328fe3bb
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08895582B2
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