Triethylamine → HCID 47451638, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13](C)C)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(C(N2C=CN=C2)=O)C=CN=[CH:17]1.Cl.[CH3:29][O:30][NH:31][CH3:32].C(N(CC)CC)C>C(Cl)Cl>[CH3:29][O:30][N:31]([CH3:32])[C:10](=[O:12])[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:13])[CH3:17]Participants
Conditions
- Temperature
- 20 °C
Procedure
To a solution of (S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (5.86 g, 27.0 mmol) in DCM (100 mL) at 0° C. was added portion wise di(1H-imidazol-1-yl)methanone (4.81 g, 29.7 mmol). Cold bath was removed and the reaction was stirred at 20° C. for 30 minutes. O,N-dimethylhydroxylamine hydrochloride (3.16 g, 32.4 mmol) was then added and followed by slow addition of triethylamine (3.28 g, 32.4 mmol). The reaction mixture was stirred at 20° C. for overnight (18 hr), and diluted with DCM (200 mL) and washed with HCl (1 M, 2×50 mL) and saturated NaHCO3 solution (2×50 mL), H2O (50 mL) and brine (50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give crude product (6.61 g). LCMS m/z 261.2 (M+H)+, Rt 0.77 min.
Workup
- customCold bath was removed
- stirringThe reaction mixture was stirred at 20° C. for overnight (18 hr)
- washwashed with HCl (1 M, 2×50 mL) and saturated NaHCO3 solution (2×50 mL), H2O (50 mL) and brine (50 mL)
- dry with materialThe organic was then dried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-83c80002a0e547b7801b229581a30e3a
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957068B2
Reaction notes
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