Diisopropylethylamine → (2S,5R)-6-(allyloxy)-3-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide
Reaction equation
[CH2:1]([O:4][NH:5][C@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([NH2:14])=[O:13])[C:8]([CH3:15])=[CH:7]1)[CH:2]=[CH2:3].C(N(C(C)C)C(C)C)C.[C:25](=O)(OC(Cl)(Cl)Cl)[O:26]C(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:25](=[O:26])[N:10]2[CH2:11][C@H:6]1[CH:7]=[C:8]([CH3:15])[C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2S,5R)-5-(allyloxyamino)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 85, 0.758 g, 3.59 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.507 mL, 14.35 mmol) in acetonitrile (350 mL) was cooled to below 0° C. in an ice-salt bath and added a solution of bis(trichloromethyl) carbonate (0.426 g, 1.44 mmol) in ACN (15 mL) at a rate of 0.1 mL/min. The reaction mixture was stirred at rt overnight. The solvents were evaporated at 30° C., and the crude mixture was redissolved in EtOAc. The crude organic solution was washed with sat. NaHCO3, brine, dried over MgSO4, and filtered. The organics were evaporated and the crude product was loaded onto silica gel at 30° C. and Purified via flash chromatography (80 g, 0-100% EtOAc/Hexanes), to obtain the desired product (0.700 g, 82%) as pale yellow oil.
Workup
- customThe solvents were evaporated at 30° C.
- dissolutionthe crude mixture was redissolved in EtOAc
- washThe crude organic solution was washed with sat. NaHCO3, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe organics were evaporated
- customwas loaded onto silica gel at 30° C.
- customPurified via flash chromatography (80 g, 0-100% EtOAc/Hexanes)
Sources & evidence
- ORD record
- ord-23f251a533534ba7bc5243e27c110855
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Reaction notes
Loading…