Diisopropylethylamine → (2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N,N-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide
Reaction equation
[CH2:1]([O:4][NH:5][C@@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@@H:9]([CH2:17][O:18][CH3:19])[NH:8][CH2:7]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:30](=[O:32])[N:8]2[CH2:7][C@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@H:9]2[CH2:17][O:18][CH3:19])[CH:2]=[CH2:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 142, 725 mg, 2.69 mmol) and Hunig's Base (1.880 mL, 10.77 mmol) in acetonitrile (350 mL) was cooled to below 0° C. in an ice-salt bath and then a solution of triphosgene (320 mg, 1.08 mmol) in ACN (22 mL) was added at a rate of 0.1 mL/min. The reaction was stirred overnight at rt. Upon completion of the reaction, the solvents were removed and the crude mixture was redissolved in EtOAc, washed with sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated to obtain the desired product (658 mg, 83%) as a pale yellow oil.
Workup
- customUpon completion of the reaction
- customthe solvents were removed
- dissolutionthe crude mixture was redissolved in EtOAc
- washwashed with sat. NaHCO3 and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d4551fc08ac84952aed435d11e22faf1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Reaction notes
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