Reaction equation
[C:1](N)(=O)[CH2:2][CH2:3]C(N)=O.CCN([CH:15]([CH3:17])[CH3:16])C(C)C.[C:18]([O-:25])(=[O:24])[CH2:19][CH2:20][C:21]([O-:23])=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:3]([O:22][C:21](=[O:23])[CH2:20][CH2:19][C:18]([O:25][CH2:17][CH:15]=[CH2:16])=[O:24])[CH:2]=[CH2:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 10 (380 mg, 1.1 mmol), DIPEA (1 mL, 5.7 mmol), and 11 (0.37 g, 1.2 mmol) in DMF (30 mL) was added HATU (0.43 g, 1.1 mmol) and the solution was allowed to stir for 24 h at room temperature. The solution was diluted with EtOAc (150 mL) and washed with 5% aqueous solution of LiCl (3×100 mL), 1 N HCl (1×100 mL), saturated aqueous NaHCO3 (2×100 mL), brine, dried over anhydrous Na2SO4, filtered, and concentrated to yield an pale yellow oil. This residue was further purified by column chromatography (silica gel, 3:1 Hexanes/EtOAc) to yield 12 (0.31 g, 44%) as a white foam: 1H NMR (300 MHz, CDCl3) δ 7.86-6.91 (m, 9 H), 5.82 (m, 2 H), 5.67 (m, 1 H), 5.09 (m, 4 H), 3.48 (s, 3 H), 2.73-2.28 (m, 5 H), 1.92 (m, 1 H), 1.61 (m, 1 H), 1.42 (s, 9 H), 1.27 (m, 1 H), 0.93 (m, 6 H); ESI MS m/z=626 [C35H42F3N3O4+H]+.
Workup
- washwashed with 5% aqueous solution of LiCl (3×100 mL), 1 N HCl (1×100 mL), saturated aqueous NaHCO3 (2×100 mL), brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto yield an pale yellow oil
- customThis residue was further purified by column chromatography (silica gel, 3:1 Hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-fbd95abcb25e434bbb630d83c20b514f
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06509333B2
Linked notes
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