Triethylamine → HCID 86094167, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([OH:15])=O)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl.[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl>[CH3:20][O:19][N:18]([CH3:17])[C:13]([C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)=[O:15]Participants
Procedure
To a suspension of the intermediate from step D (1.5 mmol) and N,O-dimethyhydroxylamine hydrochloride (219 mg, 2.25 mmol), in dichloromethane (20 mL) was added triethyl amine (1.04 mL, 7.5 mmol) followed by bromo(trispyrrolidin-1yl)phosphonium hexafluorophosphate (840 mg, 1.8 mmol). After stirring the reaction mixture at room temperature for 3 hours, it was quenched by the addition of 1N HCl (10 mL). The resulting mixture was extracted with DCM. The organic layer was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 70% ethyl acetate-hexanes. 1H NMR (500 MHz, CDCl3): 9.15 (d, J=1.8 Hz, 1H), 8.5 (d, J=1.8 Hz, 1H), 8.0 (s, 1H), 7.7 (d, J=9.0 Hz, 1H), 7.43 (d, J=2.2 Hz, 1H), 7.24 (dd, J=2.5, 9.0 Hz, 1H), 3.96 (s, 3H), 3.57 (s, 3H), 3.43 (s, 3H). LC-MS: 1.6 min; (M+H)=247.1.
Workup
- customit was quenched by the addition of 1N HCl (10 mL)
- extractionThe resulting mixture was extracted with DCM
- washThe organic layer was washed with saturated NaHCO3 solution
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- custom1.6 min
Sources & evidence
- ORD record
- ord-729d3e55d39d4b1a9c689735cf11e777
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625938B2
Reaction notes
Loading…