Isopropylamine → 4-(3-Hydroxy-1-azetidinyl)-N-(1-methylethyl)benzamide
Reaktionsgleichung
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=CC=C[C:11]=2N=N1.[OH:28][CH:29]1[CH2:32][N:31]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=2)[CH2:30]1.CC(N)C.C(N(CC)C(C)C)(C)C>ClCCl>[OH:28][CH:29]1[CH2:30][N:31]([C:33]2[CH:34]=[CH:35][C:36]([C:37]([NH:8][CH:12]([CH3:13])[CH3:11])=[O:39])=[CH:40][CH:41]=2)[CH2:32]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.64 g, 10.5 mmol, from Aldrich) was added to a mixture of 4-(3-hydroxyazetidin-1-yl)benzoic acid (1.93 g, 10.0 mmol), 2-propanamine (4.26 mL, 50.0 mmol) and N,N-diisopropylethylamine (3.88 g, 30.0 mmol) in dichloromethylene (10 mL). The mixture was stirred at room temperature for 2 h, and diluted with dichloromethane. The mixture was washed with aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate in hexane (gradient: 0-50%) to afford the desired product (2.21 g, 94.3%). LCMS cacld. for C13H19N2O2 (M+1)+: m/z=235.1. Found: 235.1.
Aufarbeitung
- washThe mixture was washed with aqueous NaHCO3 and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on a silica gel column
- washeluting with ethyl acetate in hexane (gradient: 0-50%)
Quellen und Nachweise
- ORD-Eintrag
- ord-4c6b88eae32f4303b98d739f894d0c71
- Quelldatensatz
- uspto-grants-2016_07
- Patentnummer
- US09382231B2
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