Dimethyl Sulfoxide → HCID 15665591, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1)=[O:17])[CH2:12][C:13]#[CH:14].C(N(CC)CC)C>ClCCl>[CH2:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][C:21](=[O:24])[CH2:22][CH2:23]1)=[O:17])[CH2:12][C:13]#[CH:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
25 ml of oxalyl chloride was added to 500 ml of dichloromethane, into which 41 ml of dimethyl sulfoxide was gradually dropped in a stream of nitrogen at a temperature of from -50° C. to -70° C. Subsequently, 10.3 g of N-(3-butynyloxycarbonyl)-4-hydroxypiperidine was dissolved in 50 ml of dichloromethane, followed by gradually dropping into the reaction mixture. Finally, 120 ml of triethylamine was dropped, followed by gradually increasing the temperature up to room temperature. The reaction solution was charged into a saturated saline solution, extracted three times with dichloromethane and dried with anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The resultant residue was purified by the use of silica gel column chromatography (elution solvent: hexane:ethyl acetate=3.1), thereby obtaining 8.9 g of the intended compound.
Workup
- additionwas gradually dropped in a stream of nitrogen at a temperature of from -50° C. to -70° C
- additionThe reaction solution was charged into a saturated saline solution
- extractionextracted three times with dichloromethane
- dry with materialdried with anhydrous magnesium sulfate
- distillationafter which the solvent was distilled off under reduced pressure
- customThe resultant residue was purified by the use of silica gel column chromatography (elution solvent: hexane:ethyl acetate=3.1)
Sources & evidence
- ORD record
- ord-f7452d85324747cc8154c41921e25345
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05482937
Reaction notes
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