Diisopropylethylamine → (5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione
Reaction equation
Cl.[CH3:2][Si:3]([C:6]#[C:7][C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=1)([CH3:5])[CH3:4].[CH3:14][C@@:15]1([CH2:22][S:23](Cl)(=[O:25])=[O:24])[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:14][C@:15]1([CH2:22][S:23]([N:11]2[CH2:10][CH:9]=[C:8]([C:7]#[C:6][Si:3]([CH3:4])([CH3:5])[CH3:2])[CH2:13][CH2:12]2)(=[O:25])=[O:24])[NH:16][C:17](=[O:21])[NH:18][C:19]1=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
4-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochloride (3.43 g, 15.9 mmol) was stirred in THF (100 mL) with [(4S)-4-methyl-2,5-dioxoimidazolidin -4-yl]methanesulfonyl chloride (3.39 g, 15 mmol) and cooled in an ice salt bath (temperature about −10° C.). N-Ethyldiisopropylamine (5.13 mL, 30 mmol) in THF (100 mL) was added dropwise over 2 hours and the mixture stirred a further 2 hours. The reaction mixture was washed with water, the aqueous layer extracted into EtOAc (×2), the organic phases combined, washed with 2M HCl (×2), saturated bicarbonate solution (x2), followed by brine, dried (sodium sulphate) and evaporated to give the crude product (5.06 g). This was used without further purification.
Workup
- washThe reaction mixture was washed with water
- extractionthe aqueous layer extracted into EtOAc (×2)
- washwashed with 2M HCl (×2), saturated bicarbonate solution (x2)
- dry with materialdried (sodium sulphate)
- customevaporated
Sources & evidence
- ORD record
- ord-8e726a72f8194378abc4fc85de84dc91
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989620B2
Reaction notes
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