Dimethyl Sulfoxide → HCID 15665591, compound

HRID 1755664Notes

Reaction equation

HRID 1755664 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

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15665590HCID 15665590, compound

Product 1

HCID 15665591HCID 15665591, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

25 ml of oxalyl chloride was added to 500 ml of dichloromethane, into which 4 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

  1. additionwas gradually dropped in a stream of nitrogen at a temperature of from -50° C. to -70° C
  2. additionThe reaction solution was charged into a saturated saline solution
  3. extractionextracted three times with dichloromethane
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationafter which the solvent was distilled off under reduced pressure
  6. 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-def9da49c28d461b91d02b187b1996ce
Source dataset
uspto-grants-1995_08
Patent number
US05438045

Reaction notes

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